Natural Products as Platforms to Overcome Antibiotic Resistance

Chemical Reviews

Volumn 117, Issue 19, 2017, Pages 12415-12474

  Rossiter, Sean E ^a   Fletcher, Madison H ^b   Wuest, William M ^a  

^a EMORY UNIVERSITY   (United States)

^b Temple University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BACTERIA; SCAFFOLDS;

ANTIBIOTIC RESISTANCE; BIOFILM FORMATION; COMBINATORIAL APPROACH; NATURAL PRODUCTS; NON-LETHAL METHODS; PATHOGENIC BACTERIUM; SHORT-TERM SOLUTIONS; SYNTHETIC APPROACH;

ANTIBIOTICS;

ANTIINFECTIVE AGENT; BIOLOGICAL PRODUCT;

ANTIBIOTIC RESISTANCE; BACTERIUM; BIOFILM; CHEMISTRY; DRUG EFFECTS; MICROBIAL SENSITIVITY TEST;

ANTI-BACTERIAL AGENTS; BACTERIA; BIOFILMS; BIOLOGICAL PRODUCTS; DRUG RESISTANCE, MICROBIAL; MICROBIAL SENSITIVITY TESTS;

EID: 85031110235     PISSN: 00092665     EISSN: 15206890     Source Type: Journal    
DOI: 10.1021/acs.chemrev.7b00283     Document Type: Review

References (299)

1. Chem. Rev. 2017, 117, issue 18
2. Patridge, E.; Gareiss, P.; Kinch, M. S.; Hoyer, D. An Analysis of FDA-Approved Drugs: Natural Products and Their Derivatives Drug Discovery Today 2016, 21, 204-207 10.1016/j.drudis.2015.01.009
3. Neu, H. Crisis in Antibiotic Resistance Science 1992, 257, 1064-1073 10.1126/science.257.5073.1064
4. Spellberg, B.; Gilbert, D. N. The Future of Antibiotics and Resistance: A Tribute to a Career of Leadership by John Bartlett Clin. Infect. Dis. 2014, 59 (Suppl 2) 71-75 10.1093/cid/ciu392
5. Viswanathan, V. K. Off-Label Abuse of Antibiotics by Bacteria Gut Microbes 2014, 5, 3-4 10.4161/gmic.28027
6. Ventola, C. L. The Antibiotic Resistance Crisis: Part 1: Causes and Threats P T A peer-reviewed J. Formul. Manag. 2015, 40, 277-283
7. Goossens, H.; Ferech, M.; Coenen, S.; Stephens, P.; the European Sureillance of Antimicrobial Consumption Project Group Comparison of Outpatient Systemic Antibacterial Use in 2004 in the United States and 27 European Countries Clin. Infect. Dis. 2007, 44, 1091-1095 10.1086/512810
8. Boeckel, T. P. Van; Gandra, S.; Ashok, A.; Caudron, Q.; Grenfell, B. T.; Levin, S. A.; Laxminarayan, R. Global Antibiotic Consumption 2000 to 2010: An Analysis of National Pharmaceutical Sales Data Lancet Infect. Dis. 2014, 14, 742-750 10.1016/S1473-3099(14)70780-7
9. Levy, S. B.; Marshall, B. Antibacterial Resistance Worldwide: Causes, Challenges and Responses Nat. Med. 2004, 10, S122-S129 10.1038/nm1145
10. Barber, M.; Rozwadowska-dowzenko, M. Infection by Penicillin Resistant Staphylococci Lancet 1948, 252, 641-644 10.1016/S0140-6736(48)92166-7
11. Levy, S. B. Microbial Resistance to Antibiotics: An Evolving and Persistant Problem Lancet 1982, 320, 83-88 10.1016/S0140-6736(82)91701-9
12. CDC. AntibioticResistance Threats in the United States, (2013.
13. White, D. G.; Zhao, S.; Sudler, R.; Ayers, S.; Friedman, S.; Chen, S.; McDermott, P. F.; McDermott, S.; Wagner, D. D.; Meng, J. The Isolation of Antibiotic-Resistant Salmonella from Retail Ground Meats N. Engl. J. Med. 2001) 345, 1147-1154 10.1056/NEJMoa010315
14. Chiu, C.-H.; Wu, T.-L.; Su, L.-H.; Chu, C.; Chia, J.-H.; Kuo, A.-J.; Chien, M.-S.; Lin, T.-Y. The Emergence in Taiwan of Fluoroquinolone Resistance in Salmonella Enterica Serotype Choleraesuis N. Engl. J. Med. 2002, 346, 413-419 10.1056/NEJMoa012261
15. O'Neill, J. Tackling Drug-Resistant Infections Globally: Final Report and Recommendations the Review on Antimicrobial Resistance. 2016.
16. McCullough, A. R.; Parekh, S.; Rathbone, J.; Del Mar, C. B.; Hoffmann, T. C. A Systematic Review of the Public's Knowledge and Beliefs about Antibiotic Resistance J. Antimicrob. Chemother. 2016, 71, 27-33 10.1093/jac/dkv310
17. WHO Antimicrobial Resistance Bull. World Health Organ. 2014, 61, 383-394
18. Johnning, A.; Kristiansson, E.; Angelin, M.; Marathe, N.; Shouche, Y. S.; Johansson, A.; Larsson, D. G. J. Quinolone Resistance Mutations in the Faecal Microbiota of Swedish Travellers to India BMC Microbiol. 2015, 15, 235-242 10.1186/s12866-015-0574-6
19. Walsh, C. Antibiotics: Actions, Origins, Resistance; ASM Press: Washington, DC, 2003.
20. Walsh, C. T.; Wencewicz, T. A. Antibiotics: Challenges, Mechanisms, Opportunities; ASM Press: Washington, DC, 2016.
21. Bourne, C. R. Utility of the Biosynthetic Folate Pathway for Targets in Antimicrobial Discovery Antibiotics 2014, 3, 1-28 10.3390/antibiotics3010001
22. Wright, P. M.; Seiple, I. B.; Myers, A. G. The Evolving Role of Chemical Synthesis in Antibacterial Drug Discovery Angew. Chem., Int. Ed. 2014, 53, 8840-8869 10.1002/anie.201310843
23. Leech, P. N.; Schoeffel, E. W.; Kreider, H. R.; Peterson, J. B.; Geiling, E. M. K.; Coon, J. M.; Cannon, P. R.; Hagebusch, O. E. Elixir of Sulfanilamide-Massengill J. Am. Med. Assoc. 1937, 109, 1531-1539 10.1001/jama.1937.02780450035011
24. Ballentine, C. Taste of Raspberries, Taste of Death: The 1937 Elixir Sulfanilamide Incident. FDA Consumer Magazine. June 1981.
25. Coates, A. Antibiotic Resistance; Coates, A., Ed.; Springer: Heidelberg, 2012.
26. Dever, L. A. Mechanisms of Bacterial Resistance to Antibiotics Arch. Intern. Med. 1991, 151, 886 10.1001/archinte.1991.00400050040010
27. Crofts, T. S.; Gasparrini, A. J.; Dantas, G. Next-Generation Approaches to Understand and Combat the Antibiotic Resistome Nat. Rev. Microbiol. 2017, 15, 422-434 10.1038/nrmicro.2017.28
28. Munita, J. M.; Arias, C. A.; Unit, A. R.; Santiago, A. De. Mechanisms of Antibiotic Resistance Microb. Spectr. 2016, 4, 1-37 10.1128/microbiolspec.VMBF-0016-2015
29. Coates, A. Antibiotic Resistance; Coates, A., Ed.; Springer: Heidelberg, 2012; Vol. 211.
30. Munita, J. M.; Arias, C. A.; Unit, A. R.; Santiago, A. De. Mechanisms of Antibiotic Resistance Microb. Spectr. 2016, 4, 1-37 10.1128/microbiolspec.VMBF-0016-2015
31. Blair, J. M. A.; Webber, M. A.; Baylay, A. J.; Ogbolu, D. O.; Piddock, L. J. V. Molecular Mechanisms of Antibiotic Resistance Nat. Rev. Microbiol. 2015, 13, 42-51 10.1038/nrmicro3380
32. Langton, K. P.; Henderson, P. J. F.; Herbert, R. B. Antibiotic Resistance: Multidrug Efflux Proteins, a Common Transport Mechanism? Nat. Prod. Rep. 2005, 22, 439-451 10.1039/b413734p
33. McMurry, L. M.; Petrucci, R. E. J.; Levy, S. B. Active Efflux of Tetracycline Encoded by Four Genetically Different Tetracycline Resistance Determinants in Escherichia Coli Proc. Natl. Acad. Sci. U. S. A. 1980, 77, 3974-3977 10.1073/pnas.77.7.3974
34. Blair, J. M. A.; Webber, M. A.; Baylay, A. J.; Ogbolu, D. O.; Piddock, L. J. V. Molecular Mechanisms of Antibiotic Resistance Nat. Rev. Microbiol. 2015, 13, 42-51 10.1038/nrmicro3380
35. Nikaido, H. Multidrug Resistance in Bacteria Annu. Rev. Biochem. 2009, 78, 119-146 10.1146/annurev.biochem.78.082907.145923
36. Poole, K. Efflux-Mediated Antimicrobial Resistance J. Antimicrob. Chemother. 2005, 56, 20-51 10.1093/jac/dki171
37. Langton, K. P.; Henderson, P. J. F.; Herbert, R. B. Antibiotic Resistance: Multidrug Efflux Proteins, a Common Transport Mechanism? Nat. Prod. Rep. 2005, 22, 439-451 10.1039/b413734p
38. Floss, H. G.; Yu, T. W. Rifamycin-Mode of Action, Resistance, and Biosynthesis Chem. Rev. 2005, 105, 621-632 10.1021/cr030112j
39. Mingeot-Leclercq, M. P.; Glupczynski, Y.; Tulkens, P. M. Aminoglycosides: Activity and Resistance Antimicrob. Agents Chemother. 1999, 43, 727-737
40. Phillips, I.; Acar, J.; Bergan, T.; Degener, J.; Baquero, F.; Forsgren, A.; Schito, G.-C.; Wiedemann, B. Methods for the Determination of Susceptibility of Bacteria to Antimicrobial Agents. Terminology Clin. Microbiol. Infect. 1998, 4, 291-296 10.1111/j.1469-0691.1998.tb00061.x
41. Mendelson, M.; Balasegaram, M.; Jinks, T.; Pulcini, C.; Sharland, M. Antibiotic Resistance Has a Language Problem Nature 2017, 545, 23-25 10.1038/545023a
42. Repka, L. M.; Chekan, J. R.; Nair, S. K.; van der Donk, W. A. Mechanistic Understanding of Lanthipeptide Biosynthetic Enzymes Chem. Rev. 2017, 117, 5457-5520 10.1021/acs.chemrev.6b00591
43. Lovering, F.; Bikker, J.; Humblet, C. Escape from Flatland: Increasing Saturation as an Approach to Improving Clinical Success J. Med. Chem. 2009, 52, 6752-6756 10.1021/jm901241e
44. Lovering, F. Escape from Flatland 2: Complexity and Promiscuity MedChemComm 2013, 4, 515-519 10.1039/c2md20347b
45. Pawlowski, A. C.; Johnson, J. W.; Wright, G. D. Evolving Medicinal Chemistry Strategies in Antibiotic Discovery Curr. Opin. Biotechnol. 2016, 42, 108-117 10.1016/j.copbio.2016.04.006
46. Lipinski, C. A.; Lombardo, F.; Dominy, B. W.; Feeney, P. J. Experimental and Computational Approaches to Estimate Solubility and Permeability in Drug Discovery and Development Settings Adv. Drug Delivery Rev. 2001, 46, 3-26 10.1016/S0169-409X(00)00129-0
47. Galloway, W. R. J. D.; Bender, A.; Welch, M.; Spring, D. R. The Discovery of Antibacterial Agents Using Diversity-Oriented Synthesis Chem. Commun. 2009, 18, 2446-2462 10.1039/b816852k
48. Schreiber, S. L. Target-Oriented and Diversity-Oriented Organic Synthesis in Drug Discovery Science 2000, 287, 1964-1969 10.1126/science.287.5460.1964
49. Huigens, R. W., III; Morrison, K. C.; Hicklin, R. W.; Flood, T. A., Jr; Richter, M. F.; Hergenrother, P. J. A Ring-Distortion Strategy to Construct Stereochemically Complex and Structurally Diverse Compounds from Natural Products Nat. Chem. 2013, 5, 195-202 10.1038/nchem.1549
50. Rafferty, R. J.; Hicklin, R. W.; Maloof, K. A.; Hergenrother, P. J. Synthesis of Complex and Diverse Compounds through Ring Distortion of Abietic Acid Angew. Chem., Int. Ed. 2014, 53, 220-224 10.1002/anie.201308743
51. Morrison, K. C.; Hergenrother, P. J. Natural Products as Starting Points for the Synthesis of Complex and Diverse Compounds Nat. Prod. Rep. 2014, 31, 6-14 10.1039/C3NP70063A
52. Allred, T. K.; Manoni, F.; Harran, P. G. Exploring the Boundaries of " Practical ": De Novo Syntheses of Complex Natural Product-Based Drug Candidates Chem. Rev. 2017, 10.1021/acs.chemrev.7b00126
53. Chou, T.-C.; Dong, H.; Rivkin, A.; Yoshimura, F.; Gabarda, A. E.; Cho, Y. S.; Tong, W. P.; Danishefsky, S. J. Design and Total Synthesis of a Superior Family of Epothilone Analogues which Eliminate Xenograft Tumors to a Nonrelapsable State Angew. Chem. 2003, 115, 4910-4915 10.1002/ange.200352361
54. Rivkin, A.; Chou, T.-C.; Danishefsky, S. J. On the Remarkable Antitumor Properties of Fludelone: How we Got There Angew. Chem., Int. Ed. 2005, 44, 2838-2850 10.1002/anie.200461751
55. Danishefsky, S. On the potential of natural products in the discovery of pharma leads: A case for reassessment Nat. Prod. Rep. 2010, 27, 1114-1116 10.1039/c003211p
56. Wender, P. A.; Quiroz, R. V.; Stevens, M. C. Function through Synthesis-Informed Design Acc. Chem. Res. 2015, 48, 752-760 10.1021/acs.accounts.5b00004
57. Wender, P. A.; Verma, V. A.; Paxton, T. J.; Pillow, T. H. Function-Oriented Synthesis, Step Economy, and Drug Design Acc. Chem. Res. 2008, 41, 40-49 10.1021/ar700155p
58. Cordier, C.; Morton, D.; Murrison, S.; Nelson, A.; O'Leary-Steele, C. Natural Products as an Inspiration in the Diversity-Oriented Synthesis of Bioactive Compound Libraries Nat. Prod. Rep. 2008, 25, 719-737 10.1039/b706296f
59. Thomas, G. L.; Spandl, R. J.; Glansdorp, F. G.; Welch, M.; Bender, A.; Cockfield, J.; Lindsay, J. A.; Bryant, C.; Brown, D. F. J.; Loiseleur, O. et al. Anti-MRSA Agent Discovery Using Diversity-Oriented Synthesis Angew. Chem., Int. Ed. 2008, 47 (15) 2808-2812 10.1002/anie.200705415
60. Socha, A. M.; Tan, N. Y.; Laplante, K. L.; Sello, J. K. Diversity-Oriented Synthesis of Cyclic Acyldepsipeptides Leads to the Discovery of a Potent Antibacterial Agent Bioorg. Med. Chem. 2010, 18, 7193-7202 10.1016/j.bmc.2010.08.032
61. Paciaroni, N. G.; Ratnayake, R.; Matthews, J. H.; Norwood, V. M., IV; Arnold, A. C.; Dang, L. H.; Luesch, H.; Huigens, R. W., III A Tryptoline Ring-Distortion Strategy Leads to Complex and Diverse Biologically Active Molecules from the Indole Alkaloid Yohimbine Chem.-Eur. J. 2017, 23, 4327-4335 10.1002/chem.201604795
62. McGuire, J. M.; Bunch, R. L.; Anderson, R. C.; Boaz, H. E.; Flynn, E. H.; Powell, H. M.; Smith, J. W. Ilotycin, a New Antibiotic Antibiot. Chemother. 1952, 2, 281-283
63. Erythromycin: Another Antibiotic. Lancet 1952, 260, 232-233. 10.1016/S0140-6736(52)91557-2
64. Erythromycin, New and Promising Antibiotic. N. Engl. J. Med. 1952, 247, 267-269. 10.1056/NEJM195208142470710
65. Wiley, P. F.; Gerzon, K.; Flynn, E. H.; Sigal, M. V., Jr.; Weaver, O.; Quarck, U. C.; Chauvette, R. R.; Monahan, R. Erythromycin. X. Structure of Erythromycin J. Am. Chem. Soc. 1957, 79, 6062-6070 10.1021/ja01579a059
66. Harris, D. R.; McGeachin, S. G.; Mills, H. H. The Structure and Stereochemistry of Erythromycin A Tetrahedron Lett. 1965, 6, 679-685 10.1016/S0040-4039(00)90018-2
67. Celmer, W. D. Stereochemical Problems in Macrolide Antibiotics Pure Appl. Chem. 1971, 28, 413-453 10.1351/pac197128040413
68. Contreras, A.; Vázquez, D. Cooperative and Antagonistic Interactions of Peptidyl-tRNA and Antibiotics with Bacterial Ribosomes Eur. J. Biochem. 1977, 74, 539-547 10.1111/j.1432-1033.1977.tb11422.x
69. Andersson, S.; Kurland, C. G. Elongating Ribosomes in Vivo Are Refractory to Erythromycin Biochimie 1987, 69, 901-904 10.1016/0300-9084(87)90218-5
70. Dunkle, J. A.; Xiong, L.; Mankin, A. S.; Cate, J. H. D. Structures of the Escherichia coli Ribosome with Antibiotics Bound near the Peptidyl Transferase Center Explain Spectra of Drug Action Proc. Natl. Acad. Sci. U. S. A. 2010, 107, 17152-17157 10.1073/pnas.1007988107
71. Sutcliffe, J.; Tait-Kamradt, A.; Wondrack, L. Streptococcus pneumoniae and Streptococcus pyogenes Resistant to Macrolides but Sensitive to Clindamycin: A Common Resistance Pattern Mediated by an Efflux System Antimicrob. Agents Chemother. 1996, 40, 1817-1824
72. Felmingham, D.; Cantón, R.; Jenkins, S. G. Regional Trends in Beta-Lactam, Macrolide, Fluoroquinolone and Telithromycin Resistance among Streptococcus pneumoniae Isolates 2001-2004 J. Infect. 2007, 55, 111-118 10.1016/j.jinf.2007.04.006
73. Wierzbowski, A. K.; Nichol, K.; Laing, N.; Hisanaga, T.; Nikulin, A.; Karlowsky, J. A.; Hoban, D. J.; Zhanel, G. G. Macrolide Resistance Mechanisms among Streptococcus pneumoniae Isolated over 6 Years of Canadian Respiratory Organism Susceptibility Study (CROSS) (1998-2004) J. Antimicrob. Chemother. 2007, 60, 733-740 10.1093/jac/dkm273
74. Lubelski, J.; Konings, W. N.; Driessen, A. J. M. Distribution and Physiology of ABC-Type Transporters Contributing to Multidrug Resistance in Bacteria Microbiol. Mol. Biol. Rev. 2007, 71, 463-476 10.1128/MMBR.00001-07
75. Kobayashi, N.; Nishino, K.; Yamaguchi, A. Novel Macrolide-Specific ABC-Type Efflux Transporter in Escherichia coli J. Bacteriol. 2001, 183, 5639-5644 10.1128/JB.183.19.5639-5644.2001
76. Ojo, K. K.; Striplin, M. J.; Ulep, C. C.; Close, N. S.; Zittle, J.; Luis, H.; Bernardo, M.; Leitao, J.; Roberts, M. C. Staphylococcus Efflux msr(A) Gene Characterized in Streptococcus, Enterococcus, Corynebacterium, and Pseudomonas Isolates Antimicrob. Agents Chemother. 2006, 50, 1089-1091 10.1128/AAC.50.3.1089-1091.2006
77. Blair, J. M. A.; Piddock, L. J. V. Structure, Function, and Inhibition of RND Efflux Pumps in Gram-Negative Bacteria: An Update Curr. Opin. Microbiol. 2009, 12, 512-519 10.1016/j.mib.2009.07.003
78. Chollet, R.; Chevalier, J.; Bryskier, A.; Pagès, J. M. The AcrAB-TolC Pump Is Involved in Macrolide Resistance but Not in Telithromycin Efflux in Enterobacter aerogenes and Escherichia coli Antimicrob. Agents Chemother. 2004, 48, 3621-3624 10.1128/AAC.48.9.3621-3624.2004
79. Wehmeier, C.; Schuster, S.; Fähnrich, E.; Kern, W. V.; Bohnert, J. A. Site-Directed Mutagenesis Reveals Amino Acid Residues in the Escherichia coli RND Efflux Pump AcrB That Confer Macrolide Resistance Antimicrob. Agents Chemother. 2009, 53, 329-330 10.1128/AAC.00921-08
80. Canu, A.; Malbruny, B.; Coquemont, M.; Davies, T. A.; Appelbaum, P. C.; Leclercq, R. Diversity of Ribosomal Mutations Conferring Resistance to Macrolides, Clindamycin, Streptogramin, and Telithromycin in Streptococcus pneumoniae Antimicrob. Agents Chemother. 2002, 46, 125-131 10.1128/AAC.46.1.125-131.2002
81. Björkholm, B.; Sjölund, M.; Falk, P. G.; Berg, O. G.; Engstrand, L.; Andersson, D. I. Mutation Frequency and Biological Cost of Antibiotic Resistance in Helicobacter pylori Proc. Natl. Acad. Sci. U. S. A. 2001, 98, 14607-14612 10.1073/pnas.241517298
82. Allen, N. E. Macrolide Resistance in Staphylococcus aureus: Induction of Macrolide-Resistant Protein Synthesis Antimicrob. Agents Chemother. 1977, 11, 661-668 10.1128/AAC.11.4.661
83. Allen, N. E. Macrolide Resistance in Staphylococcus aureus: Inducers of Macrolide Resistance Antimicrob. Agents Chemother. 1977, 11, 669-674 10.1128/AAC.11.4.669
84. Pestka, S.; Vince, R.; Lemahieu, R.; Weiss, F.; Fern, L.; Unowsky, J. Induction of Erythromycin Resistance in Staphylococcus aureus by Erythromycin Derivatives Antimicrob. Agents Chemother. 1976, 9, 128-130 10.1128/AAC.9.1.128
85. Weisblum, B. Insights into Erythromycin Action from Studies of Its Activity as Inducer of Resistance Antimicrob. Agents Chemother. 1995, 39, 797-805 10.1128/AAC.39.4.797
86. Weisblum, B.; Siddhikol, C.; Lai, C. J.; Demohn, V. Erythromycin-Inducible Resistane in Staphylococcus aureus: Requirements for Induction J. Bacteriol. 1971, 106, 835-847
87. Ounissi, H.; Courvalin, P. Nucleotide Sequence of the Gene ereA Encoding the Erythromycin Esterase in Escherichia coli Gene 1985, 35, 271-278 10.1016/0378-1119(85)90005-8
88. Arthur, M.; Autissier, D.; Courvalin, P. Analysis of the Nucleotide Sequence of the ereB Gene Encoding the Erythromycin Esterase Type II Nucleic Acids Res. 1986, 14, 4987-4999 10.1093/nar/14.12.4987
89. NDM-1, and a Novel Erythromycin Esterase Gene Carried on a Unique Genetic Structure in Klebsiella pneumoniae Sequence Type 14 from India Antimicrob. Agents Chemother. 2009, 53, 5046-5054 10.1128/AAC.00774-09
90. Morar, M.; Pengelly, K.; Koteva, K.; Wright, G. D. Mechanism and Diversity of the Erythromycin Esterase Family of Enzymes Biochemistry 2012, 51, 1740-1751 10.1021/bi201790u
91. U.S. Food and Drug Adminstration. Drugs@FDA: FDA ApprovedDrug Products. https://www.accessdata.fda.gov/scripts/cder/daf/.
92. Kurath, P.; Jones, P. H.; Egan, R. S.; Perun, T. J. Acid Degradation of Erythromycin A and Erythromycin B Experientia 1971, 27, 362 10.1007/BF02137246
93. Morimoto, S.; Takahashi, T.; Watanabe, Y.; Omura, S. Chemical Modification of Erythromycins. I. Synthesis and Antibacterial Activity of 6-O-Methylerythromycins A J. Antibiot. 1984, 37, 187-189 10.7164/antibiotics.37.187
94. Djokic, S.; Kobrehel, G.; Lazarevski, G.; Lopotar, N.; Tamburasev, Z.; Kamenar, B.; Nagl, A.; Vickovic, I. Erythromycin Series. Part 11. Ring Exansion of Erythromycin A Oxime by the Beckmann Rearrangement J. Chem. Soc., Perkin Trans. 1 1986, 1881-1890 10.1039/P19860001881
95. Farrell, D. J.; Flamm, R. K.; Sader, H. S.; Jones, R. N. Results from the Solithromycin International Surveillance Program (2014) Antimicrob. Agents Chemother. 2016, 60, 3662-3668 10.1128/AAC.00185-16
96. Baker, W. R.; Clark, J. D.; Stephens, R. L.; Kim, K. H. Modification of Macrolide Antibiotics. Synthesis of 11-Deoxy-11-(Carboxyamino)-6-O-Methylerythromycin A 11,12-(Cyclic Esters) via an Intramolecular Michael Reaction of O-Carbamates with an Alpha,beta-Unsaturated Ketone J. Org. Chem. 1988, 53, 2340-2345 10.1021/jo00245a038
97. Bertrand, D.; Bertrand, S.; Neveu, E.; Fernandes, P. Molecular Characterization of Off-Target Activities of Telithroycin: A Potential Role for Nicotinic Acetycholine Receptors Antimicrob. Agents Chemother. 2010, 54, 5399-5402 10.1128/AAC.00840-10
98. U.S. Food and Drug Adminstration. FDA Briefing Document: Solithromycin Oral Capsule and Injection. (2016.
99. Owens, B. Solithromycin Rejection Chills Antibiotic Sector Nat. Biotechnol. 2017) 35, 187-188 10.1038/nbt0317-187
100. Corey, E. J.; Hopkins, P. B.; Kim, S.; Yoo, S.-E.; Nambiar, K. P.; Falck, J. R. Total Synthesis of Erythromycins. 5. Total Synthesis of Erythronolide A J. Am. Chem. Soc. 1979, 101, 7131-7134 10.1021/ja00517a088
101. Corey, E. J.; Kim, S.; Yoo, S.-E.; Nicolaou, K. C.; Melvin, L. S., Jr.; Lett, R.; Sheldrake, P. W., Jr; Brunelle, D. J.; Falck, J. R.; Trybulski, E. J. et al. Total Synthesis of Erythromycins. 4. Total Synthesis of Erythronolide B J. Am. Chem. Soc. 1978, 100, 4620-4622 10.1021/ja00482a063
102. Woodward, R. B.; Logusch, E.; Nambiar, K. P.; Sakan, K.; Ward, D. E.; Auyeung, B. W.; Balaram, P.; Browne, L. J.; Card, P. J.; Chen, C. H. et al. Asymmetric Total Synthesis of Erythromycin. 1. Synthesis of an Erythronolide A Seco Acid Derivative via Asymmetric Induction J. Am. Chem. Soc. 1981, 103, 3210-3213 10.1021/ja00401a049
103. Woodward, R. B.; Logusch, E.; Nambiar, K. P.; Sakan, K.; Ward, D. E.; Au-Yeung, B. W.; Balaram, P.; Browne, L. J.; Card, P. J.; Chen, C. H. et al. Asymmetric Total Synthesis of Erythromycin. 2. Synthesis of an Erythronolide A Lactone System J. Am. Chem. Soc. 1981, 103, 3213-3215 10.1021/ja00401a050
104. Woodward, R. B.; Logusch, E.; Nambiar, K. P.; Sakan, K.; Ward, D. E.; Au-Yeung, B. W.; Balaram, P.; Browne, L. J.; Card, P. J.; Chen, C. H. Asymmetric Total Synthesis of Erythromycin. 3. Total Synthesis of Erythromycin J. Am. Chem. Soc. 1981, 103, 3215-3217 10.1021/ja00401a051
105. Martin, S. F.; Hida, T.; Kym, P. R.; Loft, M.; Hodgson, A. The Asymmetric Synthesis of Erythromycin B J. Am. Chem. Soc. 1997, 119, 3193-3194 10.1021/ja963575y
106. Hergenrother, P. J.; Hodgson, A.; Judd, A. S.; Lee, W.-C.; Martin, S. F. An Abiotic Strategy for the Enantioselective Synthesis of Erythromycin B Angew. Chem., Int. Ed. 2003, 42, 3278-3281 10.1002/anie.200351136
107. Breton, P.; Hergenrother, P. J.; Hida, T.; Hodgson, A.; Judd, A. S.; Kraynack, E.; Kym, P. R.; Lee, W.-C.; Loft, M. S.; Yamashita, M. et al. Total Synthesis of Erythromycin B Tetrahedron 2007, 63, 5709-5729 10.1016/j.tet.2007.02.044
108. Kim, H. C.; Kang, S. H. Total Synthesis of Azithromycin Angew. Chem., Int. Ed. 2009, 48, 1827-1829 10.1002/anie.200805334
109. Seiple, I. B.; Zhang, Z.; Jakubec, P.; Langlois-Mercier, A.; Wright, P. M.; Hog, D. T.; Yabu, K.; Allu, S. R.; Fukuzaki, T.; Carlsen, P. N. et al. A Platform for the Discovery of New Macrolide Antibiotics Nature 2016, 533, 338-345 10.1038/nature17967
110. Seiple, I. B.; Hog, D. T.; Myers, A. G. Practical Protocols for the Preparation of Highly Enantioenriched Silyl Ethers of (R)-3-Hydroxypentan-2-One, Building Blocks for the Synthesis of Macrolide Antibiotics Synlett 2016, 27, 57-60 10.1055/s-0035-1560972
111. Morales, M. R.; Mellem, K. T.; Myers, A. G. Pseudoephenamine: A Practical Chiral Auxiliary for Asymmetric Synthesis Angew. Chem., Int. Ed. 2012, 51, 4568-4571 10.1002/anie.201200370
112. Zhang, Z.; Kitamura, Y.; Myers, A. G. An Efficient Directed Claisen Reaction Allows for Rapid Construction of 5,6-Disubstituted 1,3-Dioxin-4-Ones Synthesis 2015, 47, 2709-2712 10.1055/s-0034-1378822
113. Boeckman, R. K., Jr.; Pruitt, J. R. A New, Highly Efficient, Selective Methodology for Formation of Medium-Ring and Macrocyclic Lactones via Intramolecular Ketene Trapping: An Application to a Convergent Synthesis of (-)-Kromycin J. Am. Chem. Soc. 1989, 111, 8286-8288 10.1021/ja00203a044
114. Zhang, Z.; Fukuzaki, T.; Myers, A. G. Synthesis of -Desosamine and Analogs by Rapid Assembly of 3-Amino Sugars Angew. Chem., Int. Ed. 2016, 55, 523-527 10.1002/anie.201507357
115. Tu, D.; Blaha, G.; Moore, P. B.; Steitz, T. A. Structures of MLSBK Antibiotics Bound to Mutated Large Ribosomal Subunits Provide a Structural Explanation for Resistance Cell 2005, 121, 257-270 10.1016/j.cell.2005.02.005
116. Andrade, R. B. Total Synthesis of Desmethyl Macrolide Antibiotics Synlett 2015, 26, 2199-2215 10.1055/s-0034-1381047
117. Velvadapu, V.; Glassford, I.; Lee, M.; Paul, T.; Debrosse, C.; Klepacki, D.; Small, M. C.; MacKerell, A. D.; Andrade, R. B. Desmethyl Macrolides: Synthesis and Evaluation of 4,10-Didesmethyl Telithromycin ACS Med. Chem. Lett. 2012, 3, 211-215 10.1021/ml200254h
118. Velvadapu, V.; Paul, T.; Wagh, B.; Klepacki, D.; Guvench, O.; MacKerell, A.; Andrade, R. B. Desmethyl Macrolides: Synthesis and Evaluation of 4,8,10-Tridesmethyl Telithromycin ACS Med. Chem. Lett. 2011, 2, 68-72 10.1021/ml1002184
119. Wagh, B.; Paul, T.; Glassford, I.; Debrosse, C.; Klepacki, D.; Small, M. C.; MacKerell, A. D.; Andrade, R. B. Desmethyl Macrolides: Synthesis and Evaluation of 4,8-Didesmethyl Telithromycin ACS Med. Chem. Lett. 2012, 3, 1013-1018 10.1021/ml300230h
120. Glassford, I.; Lee, M.; Wagh, B.; Velvadapu, V.; Paul, T.; Sandelin, G.; DeBrosse, C.; Klepacki, D.; Small, M. C.; Mackerell, A. D. et al. Desmethyl Macrolides: Synthesis and Evaluation of 4-Desmethyl Telithromycin ACS Med. Chem. Lett. 2014, 5, 1021-1026 10.1021/ml5002097
121. Gumbart, J.; Schreiner, E.; Wilson, D. N.; Beckmann, R.; Schulten, K. Mechanisms of SecM-Mediated Stalling in the Ribosome Biophys. J. 2012, 103, 331-341 10.1016/j.bpj.2012.06.005
122. Washington, A. Z.; Tapadar, S.; George, A.; Oyelere, A. K. Exploiting Translational Stalling Peptides in an Effort to Extend Azithromycin Interaction Within the Prokaryotic Ribosome Nascent Peptide Exit Tunnel Bioorg. Med. Chem. 2015, 23, 5198-5209 10.1016/j.bmc.2015.04.078
123. Liu, F.; Myers, A. G. Development of a Platform for the Discovery and Practical Synthesis of New Tetracycline Antibiotics Curr. Opin. Chem. Biol. 2016, 32, 48-57 10.1016/j.cbpa.2016.03.011
124. Brodersen, D. E.; Clemons, W. M.; Carter, A. P.; Morgan-warren, R. J.; Wimberly, B. T.; Ramakrishnan, V. The Structural Basis for the Action of the Antibiotics Tetracycline, Pactamycin, and Hygromycin B on the 30S Ribosomal Subunit Cell 2000, 103, 1143-1154 10.1016/S0092-8674(00)00216-6
125. Chopra, I.; Roberts, M. Tetracycline Antibiotics: Mode of Action, Applications, Molecular Biology, and Epidemiology of Bacterial Resistance Microbiol. Mol. Biol. Rev. 2001, 65, 232-260 10.1128/MMBR.65.2.232-260.2001
126. Connell, S. R.; Tracz, D. M.; Nierhaus, K. H.; Taylor, D. E. Ribosomal Protection Proteins and Their Mechanism of Tetracycline Resistance Antimicrob. Agents Chemother. 2003, 47, 3675-3681 10.1128/AAC.47.12.3675-3681.2003
127. Sanchez-Pescador, R.; Brown, J. T.; Roberts, M.; Urdea, M. S. Homology of the TetM with Translational Elongation Factors: Implications for Potential Modes of TetM-Conferred Tetracycline Resistance Nucleic Acids Res. 1988, 16, 1218 10.1093/nar/16.3.1218
128. Burdett, V. Purification and Characterization of Tet(M), a Protein That Renders Ribosomes Resistant to Tetracycline J. Biol. Chem. 1991, 266, 2872-2877
129. Burdett, V. Tet(M)-Promoted Release of Tetracycline from Ribosomes Is GTP Dependent J. Bacteriol. 1996, 178, 3246-3251 10.1128/jb.178.11.3246-3251.1996
130. Trieber, C. A.; Burkhardt, N.; Nierhaus, K. H.; Taylor, D. E. Ribosomal Protection from Tetracycline Mediated by Tet(O): Tet(O) Interaction with Ribosomes Is GTP-Dependent Biol. Chem. 1998, 379, 847-856 10.1515/bchm.1998.379.7.847
131. Dönhöfer, A.; Franckenberg, S.; Wickles, S.; Berninghausen, O.; Beckmann, R.; Wilson, D. N. Structural Basis for TetM-Mediated Tetracycline Resistance Proc. Natl. Acad. Sci. U. S. A. 2012, 109, 16900-16905 10.1073/pnas.1208037109
132. Li, W.; Atkinson, G. C.; Thakor, N. S.; Allas, Ü.; Lu, C.; Chan, K.-Y.; Tenson, T.; Schulten, K.; Wilson, K. S.; Hauryliuk, V. et al. Mechanism of Tetracycline Resistance by Ribosomal Protection Protein Tet(O) Nat. Commun. 2013, 4, 1477 10.1038/ncomms2470
133. Speer, B. S.; Bedzyk, L.; Salyers, A. A. Evidence That a Novel Tetracycline Resistance Gene Found on Two Bacteroides Transposons Encodes an NADP-Requiring Oxidoreductase J. Bacteriol. 1991, 173, 176-183 10.1128/jb.173.1.176-183.1991
134. Caryl, J. A.; Cox, G.; Trimble, S.; O'Neill, A. J. tet(U)" is Not a Tetracycline Resistance Determinant Antimicrob. Agents Chemother. 2012, 56, 3378-3379 10.1128/AAC.05957-11
135. Stephens, C. R.; Murai, K.; Rennhard, H. H.; Conover, L. H.; Brunings, K. J. Hydrogenolysis Studies in the Tetracycline Series-6-Deoxytetracyclines J. Am. Chem. Soc. 1958, 80, 5324-5325 10.1021/ja01552a082
136. Church, F. R.; Weiss, J. Synthesis of 7-Dimethylamino-6-Demethyl-6-Deoxytetracycline (Minocycline) via 9-Nitro-6-Demethyl-6-Deoxytetracycline J. Org. Chem. 1971, 36, 723-725 10.1021/jo00804a025
137. Martell, M. J.; Boothe, J. H. The 6-Deoxytetracyclines. VII. Alkylated Aminotetracyclines Possessing Unique Antibacterial Activity J. Med. Chem. 1967, 10, 44-46 10.1021/jm00313a009
138. Sum, P. E.; Lee, V. J.; Testa, R. T.; Hlavka, J. J.; Ellestad, G. A.; Bloom, J. D.; Gluzman, Y.; Tally, F. P. Glycylcyclines. 1. A New Generation of Potent Antibacterial Agents through Modification of 9-Aminotetracyclines J. Med. Chem. 1994, 37, 184-188 10.1021/jm00027a023
139. Olson, M. W.; Ruzin, A.; Feyfant, E.; Rush, T. S., III; O'Connell, J.; Bradford, P. A. Functional, Biophysical, and Structural Bases for Antibacterial Activity of Tigecycine Antimicrob. Agents Chemother. 2006, 50, 2156-2166 10.1128/AAC.01499-05
140. Honeyman, L.; Ismail, M.; Nelson, M. L.; Bhatia, B.; Bowser, T. E.; Chen, J.; Mechiche, R.; Ohemeng, K.; Verma, A. K.; Cannon, E. P. et al. Structure-Activity Relationship of the Aminomethylcyclines and the Discovery of Omadacycline Antimicrob. Agents Chemother. 2015, 59, 7044-7053 10.1128/AAC.01536-15
141. Paratek Announces Positive Phase 3 Study of Omadacycline in Community-Acquired Bacterial Pneumonia. April 3, 2017.
142. Paratek Announces Phase 3 Study of Oral-Only Dosing of Omadacycline Met All Primary and Secondary FDA and EMA Eficacy Endpoints in Acute Bacterial Skin Infections. July 17, 2017.
143. Gurevich, A. I.; Karapetyan, M. G.; Kolosov, M. N.; Korobko, V.; Onoprienko, V. V.; Popravko, S. A.; Shemyakin, M. Synthesis of 12a-Deoxy-5a, 6-Anhydrotetracycline. The First Total Synthesis of the Naturally Occurring Tetracycline Tetrahedron Lett. 1967, 8, 131-134 10.1016/S0040-4039(00)90501-X
144. Korst, J. J.; Johnston, J. D.; Butler, K.; Bianco, E. J.; Conover, L. H.; Woodward, R. B. The Total Synthesis of Dl-6-Demethyl-6-Deoxytetracycline J. Am. Chem. Soc. 1968, 90, 439-457 10.1021/ja01004a041
145. Muxfeldt, H.; Haas, G.; Hardtmann, G.; Kathawala, F.; Mooberry, J. B.; Vedejs, E. Tetracyclines. 9. Total Synthesis of Dl-Terramycin J. Am. Chem. Soc. 1979, 101, 689-701 10.1021/ja00497a035
146. Stork, G.; La Clair, J. J.; Spargo, P.; Nargund, R. P.; Totah, N. Stereocontrolled Synthesis of (±)-12a-Deoxytetracycline J. Am. Chem. Soc. 1996, 118, 5304-5305 10.1021/ja960434n
147. Stork, G.; Hagedorn, A. A., III 3-Benzyloxyisoxazole System in Construction of Tetracyclines J. Am. Chem. Soc. 1978, 100, 3609-3611 10.1021/ja00479a060
148. Tatsuta, K.; Yoshimoto, T.; Gunji, H.; Okado, Y.; Takahashi, M. The First Total Synthesis of Natural (-)-Tetracycline Chem. Lett. 2000, 29, 646-647 10.1246/cl.2000.646
149. Charest, M. G.; Lerner, C. D.; Brubaker, J. D.; Siegel, D. R.; Myers, A. G. A Convergent Enantioselective Route to Structurally Diverse 6-Deoxytetracycline Antibiotics Science 2005, 308, 395-398 10.1126/science.1109755
150. Wilson, R. M.; Danishefsky, S. J. Small Molecule Natural Products in the Discovery of Therapeutic Agents: The Synthesis Connection J. Org. Chem. 2006, 71, 8329-8351 10.1021/jo0610053
151. Myers, A. G.; Movassaghi, M.; Zheng, B. Single-Step Process or the Reductive Deoxygenation of Unhindered Alcohols J. Am. Chem. Soc. 1997, 119, 8572-8573 10.1021/ja971768v
152. Brubaker, J. D.; Myers, A. G. A Practical, Enantioselective Synthetic Route to a Key Precursor to the Tetracycline Antibiotics Org. Lett. 2007, 9, 3523-3525 10.1021/ol071377d
153. Kummer, D. A.; Li, D.; Dion, A.; Myers, A. G. A Practical, Convergent Route to the Key Precursor to the Tetracycline Antibiotics Chem. Sci. 2011, 2, 1710-1718 10.1039/c1sc00303h
154. Zhang, W. Y.; Hogan, P. C.; Chen, C. L.; Niu, J.; Wang, Z.; Lafrance, D.; Gilicky, O.; Dunwoody, N.; Ronn, M. Process Research and Development of an Enantiomerically Enriched Allyic Amine, One of the Key Intermediates for the Manufacture of Synthetic Tetracyclines Org. Process Res. Dev. 2015, 19, 1784-1795 10.1021/acs.oprd.5b00274
155. Zhang, W.-Y.; Chen, C.-L.; HE, M.; Zhu, Z.; Hogan, P.; Gilicky, O.; Dunwoody, N.; Ronn, M. Process Research and Development of TP-808: A Key Intermediate for the Manufacture of Synthetic Tetracyclines Org. Process Res. Dev. 2017, 21, 377-386 10.1021/acs.oprd.7b00003
156. Sun, C.; Wang, Q.; Brubaker, J. D.; Wright, P. M.; Lerner, C. D.; Noson, K.; Charest, M.; Siegel, D. R.; Wang, Y.; Myers, A. G. A Robust Platform for the Synthesis of New Tetracycline Antibiotics J. Am. Chem. Soc. 2008, 130, 17913-17927 10.1021/ja806629e
157. Sun, C.; Hunt, D. K.; Chen, C. L.; Deng, Y.; He, M.; Clark, R. B.; Fyfe, C.; Grossman, T. H.; Sutcliffe, J. A.; Xiao, X. Y. Design, Synthesis, and Biological Evaluation of Hexacyclic Tetracyclines as Potent, Broad Spectrum Antibacterial Agents J. Med. Chem. 2015, 58, 4703-4712 10.1021/acs.jmedchem.5b00262
158. Liu, F.; Wright, P. M.; Myers, A. G. Diastereoselective Michael-Claisen Cyclizations of γ-Oxa-A,β-Unsaturated Ketones En Route to 5-Oxatetracyclines Org. Lett. 2017, 19, 206-209 10.1021/acs.orglett.6b03491
159. Xiao, X.-Y.; Hunt, D. K.; He, M.; Achorn, C.; Chen, C. L.; Deng, Y.; Fyfe, C.; Grossman, T. H.; Hogan, P. C.; O'Brien, W. J.; Clark, R. B. et al. Fluorocyclines. 1. 7-Fluoro-9-Pyrrolidinoacetamido-6-Demethyl-6- Deoxytetracycline: A Potent, Broad Spectrum Antibacterial Agent J. Med. Chem. 2012, 55, 597 10.1021/jm201465w
160. Clark, R. B.; Hunt, D. K.; He, M.; Achorn, C.; Chen, C.-L.; Deng, Y.; Fyfe, C.; Grossman, T. H.; Hogan, P. C.; O'Brien, W. J. et al. Fluorocyclines. 2. Optimization of the C-9 Side-Chain for Antibacterial Activity and Oral Efficacy J. Med. Chem. 2012, 55, 606-622 10.1021/jm201467r
161. Ronn, M.; Zhu, Z.; Hogan, P. C.; Zhang, W. Y.; Niu, J.; Katz, C. E.; Dunwoody, N.; Gilicky, O.; Deng, Y.; Hunt, D. K. et al. Process R&D of Eravacycline: The First Fully Synthetic Fluorocycline in Clinical Development Org. Process Res. Dev. 2013, 17, 838-845 10.1021/op4000219
162. Grossman, T. H.; Starosta, A. L.; Fyfe, C.; O'Brien, W.; Rothstein, D. M.; Mikolajka, A.; Wilson, D. N.; Sutcliffe, J. A. Target- and Resistance-Based Mechanistic Studies with TP-434, a Novel Fluorocycline Antibiotic Antimicrob. Agents Chemother. 2012, 56, 2559-2564 10.1128/AAC.06187-11
163. Solomkin, J.; Evans, D.; Slepavicius, A.; Lee, P.; Marsh, A.; Tsai, L.; Sutcliffe, J. A.; Horn, P. Assessing the Efficacy and Safety of Eravacycline vs Ertapenem in Complicated Intra-Abdominal Infections in the Investigating Gram-Negative Infections Treated With Eravacycline (IGNITE 1) Trial: A Randomized Clinical Trial JAMA Surg. 2017, 152, E1-E9 10.1001/jamasurg.2016.4237
164. Hutchison, R. D.; Steyn, P. S.; van Rensburg, S. J. Viridicatumtoxin, a New Mycotoxin from Penicillium Viridicatum Westling Toxicol. Appl. Pharmacol. 1973, 24, 507-509 10.1016/0041-008X(73)90057-4
165. Zheng, C.-J.; Yu, H.-E.; Kim, E.-H.; Kim, W.-G. Viridicatumtoxin B, a New Anti-MRSA Agent from Penicillium Sp. FR11 J. Antibiot. 2008, 61, 633-637 10.1038/ja.2008.84
166. Inokoshi, J.; Nakamura, Y.; Hongbin, Z.; Uchida, R.; Nonaka, K.; Masuma, R.; Tomoda, H. Spirohexalines, New Inhibitors of Bacterial Undecaprenyl Pyrophosphate Synthase, Produced by Penicillium Brasilianum FKI-3368 J. Antibiot. 2013, 66, 37-41 10.1038/ja.2012.83
167. Nicolaou, K. C.; Nilewski, C.; Hale, C. R. H.; Ioannidou, H. A.; Elmarrouni, A.; Koch, L. G. Total Synthesis and Structural Revision of Viridicatumtoxin B Angew. Chem., Int. Ed. 2013, 52, 8736-8741 10.1002/anie.201304691
168. Nicolaou, K. C.; Hale, C. R. H.; Nilewski, C.; Ioannidou, H. A.; Elmarrouni, A.; Nilewski, L. G.; Beabout, K.; Wang, T. T.; Shamoo, Y. Total Synthesis of Viridicatumtoxin B and Analogues Thereof: Strategy Evolution, Structural Revision, and Biological Evaluation J. Am. Chem. Soc. 2014, 136, 12137-12160 10.1021/ja506472u
169. Nicolaou, K. C.; Liu, G.; Beabout, K.; McCurry, M. D.; Shamoo, Y. Asymmetric Alkylation of Anthrones, Enantioselective Total Synthesis of (-)- and (+)-Viridicatumtoxins B and Analogues Thereof: Absolute Configuration and Potent Antibacterial Agents J. Am. Chem. Soc. 2017, 139, 3736-3746 10.1021/jacs.6b12654
170. McCormick, M. H.; Stark, W. M.; Pittenger, G. E.; Pittenger, R. C.; McGuire, J. M. Vancomycin, a New Antibiotic. I. Chemical and Biologic Properties Antibiot. Annu. 1955, 3, 606-611
171. Williamson, M. P.; Williams, D. H. Structure Revision of the Antibiotic Vancomycin. The Use of Nuclear Overhauser Effect Difference Spectroscopy J. Am. Chem. Soc. 1981, 103, 6580-6585 10.1021/ja00412a008
172. Harris, C. M.; Kopecka, H.; Harris, T. M. Vancomycin: Structure and Transformation to CDP-I J. Am. Chem. Soc. 1983, 105, 6915-6922 10.1021/ja00361a029
173. Levine, D. P. Vancomycin: A History Clin. Infect. Dis. 2006, 42, S5-12 10.1086/491709
174. Courvalin, P. Vancomycin Resistance in Gram-Positive Cocci Clin. Infect. Dis. 2006, 42 (Suppl 1) S25-34 10.1086/491711
175. Anderson, S. Biosynthesis of the Peptidoglycan of Bacterial Cell Walls J. Biol. Chem. 1967, 242, 3180-3190
176. Sham, L.-T.; Butler, E. K.; Lebar, M. D.; Kahne, D.; Bernhardt, T. G.; Ruiz, N. MurJ Is the Flippase of Lipid-Linked Precursors for Peptidoglycan Biogenesis Science (Washington, DC, U. S.) 2014, 345, 220-222 10.1126/science.1254522
177. Williams, D. H.; Waltho, J. P. Molecular Basis of the Activity of Antibiotics of the Vancomycin Group Biochem. Pharmacol. 1988, 37, 133-141 10.1016/0006-2952(88)90765-4
178. Nitanai, Y.; Kikuchi, T.; Kakoi, K.; Hanamaki, S.; Fujisawa, I.; Aoki, K. Crystal Structures of the Complexes between Vancomycin and Cell-Wall Precursor Analogs J. Mol. Biol. 2009, 385, 1422-1432 10.1016/j.jmb.2008.10.026
179. Périchon, B.; Courvalin, P. VanA-Type Vancomycin-Resistant Staphylococcus aureus Antimicrob. Agents Chemother. 2009, 53, 4580-4587 10.1128/AAC.00346-09
180. Arthur, M.; Molinas, C.; Courvalin, P. The VanS-VanR Two-Component Regulatory System Controls Synthesis of Depsipeptide Peptidoglycan Precursors in Enterococcus faecium BM4147 J. Bacteriol. 1992, 174, 2582-2591 10.1128/jb.174.8.2582-2591.1992
181. Wright, G. D.; Holman, T. R.; Walsh, C. T. Purification and Characterization of VanR and the Cytosolic Domain of VanS: A Two-Component Regulatory System Required for Vancomycin Resistance in Enterococcus faecium BM4147 Biochemistry 1993, 32, 5057-5063 10.1021/bi00070a013
182. Kahne, D.; Leimkuhler, C.; Lu, W.; Walsh, C. Glycopeptide and Lipoglycopeptide Antibiotics Chem. Rev. 2005, 105, 425-448 10.1021/cr030103a
183. McComas, C. C.; Crowley, B. M.; Boger, D. L. Partitioning the Loss in Vancomycin Binding Affinity for d -Ala- d -Lac into Lost H-Bond and Repulsiv Lone Pair Contributions J. Am. Chem. Soc. 2003, 125, 9314-9315 10.1021/ja035901x
184. Judice, J. K.; Pace, J. L. Semi-Synthetic Glycopeptide Antibacterials Bioorg. Med. Chem. Lett. 2003, 13, 4165-4168 10.1016/j.bmcl.2003.08.067
185. Leadbetter, M. R.; Adams, S. M.; Bazzini, B.; Fatheree, P. R.; Karr, D. E.; Krause, K. M.; Lam, B. M. T.; Linsell, M. S.; Nodwell, M. B.; Pace, J. L. et al. Hydrophobic Vancomycin Derivatives with Improved ADME Properties: Discovery of Telavancin J. Antibiot. 2004, 57, 326-336 10.7164/antibiotics.57.326
186. Krause, K. M.; Renelli, M.; Difuntorum, S.; Wu, T. X.; Debabov, D. V.; Benton, B. M. In Vitro Activity of Telavancin against Resistant Gram-Positive Bacteria Antimicrob. Agents Chemother. 2008, 52, 2647-2652 10.1128/AAC.01398-07
187. Stryjewski, M. E.; Graham, D. R.; Wilson, S. E.; O'Riordan, W.; Young, D.; Lentnek, A.; Ross, D. P.; Fowler, V. G.; Hopkins, A.; Friedland, H. D. et al. Telavancin Versus Vancomycin for the Treatment of Complicated Skin and Skin-Structure Infections Caused by Gram-Positive Organisms Clin. Infect. Dis. 2008, 46, 1683-1693 10.1086/587896
188. Allen, N. E. From Vancomycin to Oritavancin: The Discovery and Development of a Novel Lipoglycopeptide Antibiotic Anti-Infect. Agents Med. Chem. 2010, 9, 23-47 10.2174/187152110790886745
189. Sosio, M.; Stinchi, S.; Beltrametti, F.; Lazzarini, A.; Donadio, S. The Gene Cluster for the Biosynthesis of the Glycopeptide Antibiotic A40926 by Nonmuraea Species Chem. Biol. 2003, 10, 541-549 10.1016/S1074-5521(03)00120-0
190. Candiani, G.; Abbondi, M.; Borgonovi, M.; Romanò, G.; Parenti, F. In-Vitro and in-Vivo Antibacterial Activity of BI 397, a New Semi-Synthetic Glycopeptide Antibiotic J. Antimicrob. Chemother. 1999, 44, 179-192 10.1093/jac/44.2.179
191. Seltzer, E.; Dorr, M. B.; Goldstein, B. P.; Perry, M.; Dowell, J. a; Henkel, T. Once-Weekly Dalbavancin versus Standard-of-Care Antimicrobial Regimens for Treatment of Skin and Soft-Tissue Infections Clin. Infect. Dis. 2003, 37, 1298-1303 10.1086/379015
192. Boucher, H. W.; Wilcox, M.; Talbot, G. H.; Puttagunta, S.; Das, A. F.; Dunne, M. W. Once-Weekly Dalbavancin versus Daily Conventional Therapy for Skin Infection N. Engl. J. Med. 2014, 370, 2169-2179 10.1056/NEJMoa1310480
193. Sharman, G. J.; Try, A. C.; Dancer, R. J.; Cho, Y. R.; Staroske, T.; Bardsley, B.; Maguire, A. J.; Cooper, M. A.; O'Brien, D. P.; Williams, D. H. The Roles of Dimerization and Membrane Anchoring in Activity of Glycopeptide Antibiotics against Vancomycin-Resistant Bacteria J. Am. Chem. Soc. 1997, 119, 12041-12047 10.1021/ja964477f
194. Nicolaou, K. C.; Hughes, R.; Cho, S. Y.; Winssinger, N.; Smethurst, C.; Labischinski, H.; Endermann, R. Target-Accelerated Combinatorial Synthesis and Discovery of Highly Potent Antibiotics Effective Against Vancomycin-Resistant Bacteria Angew. Chem., Int. Ed. 2000, 39, 3823-3828 10.1002/1521-3773(20001103)39:21<3823::AID-ANIE3823>3.0.CO;2-3
195. Ge, M.; Chen, Z.; Onishi, H. R.; Kohler, J.; Silver, L. L.; Kerns, R.; Fukuzawa, S.; Thompson, C.; Kahne, D. Vancomycin Derivatives That Inhibit Peptidoglycan Biosynthesis Without Binding d -Ala- d -Ala Science 1999, 284, 507-511 10.1126/science.284.5413.507
196. Williams, D. H.; Bardsley, B. The Vancomycin Group of Antibiotics and the Fight against Resistant Bacteria Angew. Chem., Int. Ed. 1999, 38, 1172-1193 10.1002/(SICI)1521-3773(19990503)38:9<1172::AID-ANIE1172>3.0.CO;2-C
197. Okano, A.; Isley, N. A.; Boger, D. L. Total Syntheses of Vancomycin-Related Glycopeptide Antibiotics and Key Analogues. Chem. Rev. 2017, 10.1021/acs.chemrev.6b00820
198. Evans, D. A.; Wood, M. R.; Trotter, B. W.; Richardson, T. I.; Barrow, J. C.; Katz, J. L. Total Syntheses of Vancomcin and Eremomycin Aglycons Angew. Chem., Int. Ed. 1998, 37, 2700-2704 10.1002/(SICI)1521-3773(19981016)37:19<2700::AID-ANIE2700>3.0.CO;2-P
199. Evans, D. A.; Britton, T. C.; Ellman, J. A.; Dorow, R. L. The Asymmetric Synthesis of α-Amino Acids. Electrophilic Azidation of Chiral Imide Enolates, a Practical Approach to the Synthesis of (R)- and (S)-α-Azido Carboxylic Acids J. Am. Chem. Soc. 1990, 112, 4011-4030 10.1021/ja00166a045
200. Evans, D. A.; Evrad, D. A.; Rychnovsky, S. D.; Früh, T.; Whittingham, W. G.; DeVries, K. M. A General Approach to the Asymmetric Synthesis of Vancomycin-Related Arylglycines by Enolate Azidation Tetrahedron Lett. 1992, 33, 1189-1192 10.1016/S0040-4039(00)91892-6
201. Evans, D. A.; Ellman, J. A.; DeVries, K. M. The Oxidative Macrocyclization of Phenolic Peptides. A Biomimetic Approach to the Synthesis of the Vancomycin Family of Antibiotics J. Am. Chem. Soc. 1989, 111, 8912-8914 10.1021/ja00206a021
202. Evans, D. A.; Dinsmore, C. J. Kinetic and Thermodynamic Atropdiastereoselection in the Synthesis of the M(5-7) Tripeptide Portion of Vancomycin Tetrahedron Lett. 1993, 34, 6029-6032 10.1016/S0040-4039(00)61719-7
203. Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Catalytic Asymmetric Dihydroxylation Chem. Rev. 1994, 94, 2483-2547 10.1021/cr00032a009
204. Li, G.; Chang, H.; Sharpless, K. B. Catalytic Asymmetric Aminohydroxylation (AA) of Olefins Angew. Chem., Int. Ed. Engl. 1996, 35, 451-454 10.1002/anie.199604511
205. Nicolaou, K. C.; Natarajan, S.; Li, H.; Jain, N. F.; Hughes, R.; Solomon, M. E.; Ramanjulu, J. M.; Boddy, C. N. C.; Takayanagi, M. Total Synthesis of Vancomycin Aglycon-Part 1: Synthesis of Amino Acids 4-7 and Construction of the AB-COD Ring Skeleton Angew. Chem., Int. Ed. 1998, 37 (19) 2708-2714 10.1002/(SICI)1521-3773(19981016)37:19<2708::AID-ANIE2708>3.3.CO;2-5
206. Nicolaou, K. C.; Li, H.; Boddy, C. N. C.; Ramanjulu, J. M.; Yue, T. Y.; Natarajan, S.; Chu, X. J.; Brase, S.; Rübsam, F. Total Synthesis of Vancomycin-Part 1: Design and Development of Methodology Chem.-Eur. J. 1999, 5, 2584-2601 10.1002/(SICI)1521-3765(19990903)5:9<2584::AID-CHEM2584>3.0.CO;2-B
207. Nicolaou, K. C.; Jain, N. F.; Natarajan, S.; Hughes, R.; Solomon, M. E.; Li, H.; Ramanjulu, J. M.; Takayanagi, M.; Koumbis, A. E.; Bando, T. Total Synthesis of Vancomycin Aglycon-Part 2: Synthesis of Amino Acids 1-3 and Construction of the AB-COD-DOE Ring Skeleton Angew. Chem., Int. Ed. 1998, 37, 2714-2716 10.1002/(SICI)1521-3773(19981016)37:19<2714::AID-ANIE2714>3.0.CO;2-#
208. Nicolaou, K. C.; Takayanagi, M.; Jain, N. F.; Natarajan, S.; Koumbis, A. E.; Bando, T.; Ramanjulu, J. M. Total Synthesis of Vancomycin Aglycon-Part 3: Final Stages Angew. Chem., Int. Ed. 1998, 37, 2717-2719 10.1002/(SICI)1521-3773(19981016)37:19<2717::AID-ANIE2717>3.0.CO;2-I
209. Nicolaou, K. C.; Koumbis, A. E.; Takayanagi, M.; Natarajan, S.; Jain, N. F.; Bando, T.; Li, H.; Hughes, R. Total Synthesis of Vancomycin-Part 3: Synthesis of the Aglycon Chem.-Eur. J. 1999, 5, 2622-2647 10.1002/(SICI)1521-3765(19990903)5:9<2622::AID-CHEM2622>3.0.CO;2-T
210. Nicolaou, K. C.; Mitchell, H. J.; Jain, N. F.; Bando, T.; Hughes, R.; Winssinger, N.; Natarajan, S.; Koumbis, A. E. Total Synthesis of Vancomycin-Part 4: Attachment of the Sugar Moieties and Completion of the Synthesis Chem.-Eur. J. 1999, 5, 2648-2667 10.1002/(SICI)1521-3765(19990903)5:9<2648::AID-CHEM2648>3.0.CO;2-Q
211. Gerhard, U.; Mackay, J. P.; Maplestone, R. A.; Williams, D. H. The Role of the Sugar and Chlorine Sustituents in the Dimerization of Vancomycin Antibiotics J. Am. Chem. Soc. 1993, 115, 232-237 10.1021/ja00054a033
212. Nicolaou, K. C.; Cho, S. Y.; Hughes, R.; Winssinger, N.; Smethurst, C.; Labischinski, H.; Endermann, R. Solid- and Solution-Phase Synthesis of Vancomycin and Vancomycin Analogues with Activity against Vancomycin-Resistant Bacteria Chem.-Eur. J. 2001, 7, 3798-3823 10.1002/1521-3765(20010903)7:17<3798::AID-CHEM3798>3.0.CO;2-6
213. Boger, D. L.; Castle, S. L.; Miyazaki, S.; Wu, J. H.; Beresis, R. T.; Loiseleur, O. Vancomycin CD and DE Macrocyclization and Atropisomerism Studies J. Org. Chem. 1999, 64, 70-80 10.1021/jo980880o
214. Boger, D. L.; Borzilleri, R. M.; Nukui, S.; Beresis, R. T. Synthesis of the Vancomycin CD and DE Ring Systems J. Org. Chem. 1997, 62, 4721-4736 10.1021/jo970560p
215. Boger, D. L.; Miyazaki, S.; Kim, S. H.; Wu, J. H.; Loiseleur, O.; Castle, S. L. Diastereoselective Total Synthesis of the Vancomycin Aglycon with Ordered Atropisomer Equilibrations J. Am. Chem. Soc. 1999, 121, 3226-3227 10.1021/ja990189i
216. Boger, D. L.; Miyazaki, S.; Kim, S. H.; Wu, J. H.; Castle, S. L.; Loiseleur, O.; Jin, Q. Total Synthesis of the Vancomycin Aglycon J. Am. Chem. Soc. 1999, 121, 10004-10011 10.1021/ja992577q
217. 4]Vancomycin Aglycon: Reengineering Vancomycin for Dual d -Ala- d -Ala and d -Ala- d -Lac Binding J. Am. Chem. Soc. 2006, 128, 2885-2892 10.1021/ja0572912
218. 4]Vancomycin Aglycon, and Related Key Compounds: Reengineering Vancomycin for Dual d -Ala- d -Ala and d -Ala- d -Lac Binding J. Am. Chem. Soc. 2012, 134, 1284-1297 10.1021/ja209937s
219. 4]Vancomycin and Its 4-Chlorobiphenyl)methyl Derivative: Impact of Peripheral Modifications on Vancomycin Analogues Redesigned for Dual d -Ala- d -Ala and d -Ala- d -Lac Binding J. Am. Chem. Soc. 2014, 136, 13522-13525 10.1021/ja507009a
220. 4]vancomycin, and Their (4-Chlorobiphenyl)methyl Derivatives: Synergistic Binding Pocket and Peripheral Modificat J. Am. Chem. Soc. 2015, 137, 3693-3704 10.1021/jacs.5b01008
221. Losey, H. C.; Jiang, J.; Biggins, J. B.; Oberthur, M.; Ye, X. Y.; Dong, S. D.; Kahne, D.; Thorson, J. S.; Walsh, C. T. Incorporation of Glucose Analogs by GtfE and GtfD from the Vancomycin Biosynthetic Pathway to Generate Variant Glycopeptides Chem. Biol. 2002, 9, 1305-1314 10.1016/S1074-5521(02)00270-3
222. Okano, A.; Isley, N. A.; Boger, D. L. Peripheral Modifications of [ψ[CH2NH]Tpg4]vancomycin with Added Synergistic Mechanisms of Action Provide Durable and Potent Antibiotics Proc. Natl. Acad. Sci. U. S. A. 2017, E5053-E5061 10.1073/pnas.1704125114
223. Nealson, K. H.; Platt, T.; Hastings, J. W. Cellular Control of the Synthesis and Activity of the Bacterial Luminescent System J. Bacteriol. 1970, 104, 313-322
224. Eberhard, A.; Burlingame, A. L.; Eberhard, C.; Kenyon, G. L.; Nealson, K. H.; Oppenheimer, N. J. Structural Identification of Autoinducer of Photobacterium Fischeri Luciferase Biochemistry 1981, 20, 2444-2449 10.1021/bi00512a013
225. Fuqua, W. C.; Winans, S. C.; Greenberg, E. P. Quorum Sensing in Bacteria: The LuxR-LuxI Family of Cell Density-Responsive Transcriptional Regulators J. Bacteriol. 1994, 176, 269-275 10.1128/jb.176.2.269-275.1994
226. Fuqua, C.; Winans, S. C.; Greenberg, E. P. CENSUS AND CONSENSUS IN BACTERIAL ECOSYSTEMS: The LuxR-LuxI Family of Quorum-Sensing Transcriptional Regulators Annu. Rev. Microbiol. 1996, 50, 727-751 10.1146/annurev.micro.50.1.727
227. Surette, M. G.; Miller, M. B.; Bassler, B. L. Quorum Sensing in Escherichia coli, Salmonella typhimurium, and Vibrio harveyi: A New Family of Genes Responsible for Autoinducer Production Proc. Natl. Acad. Sci. U. S. A. 1999, 96, 1639-1644 10.1073/pnas.96.4.1639
228. Bassler, B. L. How Bacteria Talk to Each Other: Regulation of Gene Expression by Quorum Sensing Curr. Opin. Microbiol. 1999, 2, 582-587 10.1016/S1369-5274(99)00025-9
229. Bassler, B. L.; Losick, R. Bacterially Speaking Cell 2006, 125, 237-246 10.1016/j.cell.2006.04.001
230. Waters, C. M.; Bassler, B. L. Quorum Sensing: Communication in Bacteria Annu. Rev. Cell Dev. Biol. 2005, 21, 319-346 10.1146/annurev.cellbio.21.012704.131001
231. Bassler, B. L. Small Talk: Cell-to-Cell Communication in Bacteria Cell 2002, 109, 421-424 10.1016/S0092-8674(02)00749-3
232. Diggle, S. P.; Matthijs, S.; Wright, V. J.; Fletcher, M. P.; Chhabra, S. R.; Lamont, I. L.; Kong, X.; Hider, R. C.; Cornelis, P.; Cámara, M. et al. The Pseudomonas aeruginosa 4-Quinolone Signal Molecules HHQ and PQS Play Multifunctional Roles in Quorum Sensing and Iron Entrapment Chem. Biol. 2007, 14, 87-96 10.1016/j.chembiol.2006.11.014
233. Withers, H.; Swift, S.; Williams, P. Quorum Sensing as an Integral Component of Gene Regulatory Networks in Gram-Negative Bacteria Curr. Opin. Microbiol. 2001, 4, 186-193 10.1016/S1369-5274(00)00187-9
234. Wilson, J. W.; Schurr, M. J.; LeBlanc, C. L.; Ramamurthy, R.; Buchanan, K. L.; Nickerson, C. A. Mechanisms of Bacterial Pathogenicity Postgrad. Med. J. 2002, 78, 216-224 10.1136/pmj.78.918.216
235. Winzer, K.; Williams, P. Quorum Sensing and the Regulation of Virulence Gene Expression in Pathogenic Bacteria Int. J. Med. Microbiol. 2001, 291, 131-143 10.1078/1438-4221-00110
236. Cámara, M.; Williams, P.; Hardman, A. Controlling Infection by Tuning in and Turning down the Volume of Bacterial Small-Talk Lancet Infect. Dis. 2002, 2, 667-676 10.1016/S1473-3099(02)00447-4
237. Geske, G. D.; O'Neill, J. C.; Blackwell, H. E. Expanding Dialogues: From Natural Autoinducers to Non-Natural Analogues That Modulate Quorum Sensing in Gram-Negative Bacteria Chem. Soc. Rev. 2008, 37, 1432-1447 10.1039/b703021p
238. Praneenararat, T.; Palmer, A. G.; Blackwell, H. E. Chemical Methods to Interrogate Bacterial Quorum Sensing Pathways Org. Biomol. Chem. 2012, 10, 8189-8199 10.1039/c2ob26353j
239. Galloway, W. R. J. D.; Hodgkinson, J. T.; Bowden, S. D.; Welch, M.; Spring, D. R. Quorum Sensing in Gram-Negative Bacteria: Small-Molecule Modulation of AHL and AI-2 Quorum Sensing Pathways Chem. Rev. 2011, 111, 28-67 10.1021/cr100109t
240. Stevens, A. M.; Queneau, Y.; Soulère, L.; Bodman, S. Von; Doutheau, A. Mechanisms and Synthetic Modulators of AHL-Dependent Gene Regulation Chem. Rev. 2011, 111, 4-27 10.1021/cr100064s
241. Welsh, M. A.; Eibergen, N. R.; Moore, J. D.; Blackwell, H. E. Small Molecule Disruption of Quorum Sensing Cross-Regulation in Pseudomonas aeruginosa Causes Major and Unexpected Alterations to Virulence Phenotypes J. Am. Chem. Soc. 2015, 137, 1510-1519 10.1021/ja5110798
242. Stacy, D. M.; Welsh, M. a.; Rather, P. N.; Blackwell, H. E. Attenuation of Quorum Sensing in the Pathogen Acinetobacter baumannii Using Non-Native N-Acyl Homoserine Lactonres ACS Chem. Biol. 2012, 7, 1719-1728 10.1021/cb300351x
243. Huse, H.; Whiteley, M. 4-Quinolones: Smart Phones of the Microbial World Chem. Rev. 2011, 111, 152-159 10.1021/cr100063u
244. Williams, P.; Cámara, M. Quorum Sensing and Environmental Adaptation in Pseudomonas aeruginosa: A Tale of Regulatory Networks and Multifunctional Signal Molecules Curr. Opin. Microbiol. 2009, 12, 182-191 10.1016/j.mib.2009.01.005
245. Borrero, N. V.; Bai, F.; Perez, C.; Duong, B. Q.; Rocca, J. R.; Jin, S.; Huigens, R. W. Phenazine Antibiotic Inspired Discovery of Potent Bromophenazine Antibacterial Agents against Staphylococcus aureus and Staphylococcus epidermidis Org. Biomol. Chem. 2014, 12, 881-886 10.1039/C3OB42416B
246. Garrison, A. T.; Abouelhassan, Y.; Norwood, V. M.; Kallifidas, D.; Bai, F.; Nguyen, M. T.; Rolfe, M.; Burch, G. M.; Jin, S.; Luesch, H. et al. Structure-Activity Relationships of a Diverse Class of Halogenated Phenazines That Targets Persistent, Antibiotic-Tolerant Bacterial Biofilms and Mycobacterium tuberculosis J. Med. Chem. 2016, 59, 3808-3825 10.1021/acs.jmedchem.5b02004
247. Abouelhassan, Y.; Garrison, A. T.; Burch, G. M.; Wong, W.; Norwood, V. M.; Huigens, R. W. Discovery of Quinoline Small Molecules with Potent Dispersal Activity against Methicillin-Resistant Staphylococcus aureus and Staphylococcus epidermidis Biofilms Using a Scaffold Hopping Strategy Bioorg. Med. Chem. Lett. 2014, 24, 5076-5080 10.1016/j.bmcl.2014.09.009
248. Garrison, A. T.; Abouelhassan, Y.; Yang, H.; Yousaf, H. H.; Nguyen, T. J.; Huigens Iii, R. W. Microwave-Enhanced Friedländer Synthesis for the Rapid Assembly of Halogenated Quinolines with Antibacterial and Biofilm Eradication Activities against Drug Resistant and Tolerant Bacteria MedChemComm 2017, 8, 720-724 10.1039/C6MD00381H
249. Thoendel, M.; Kavanaugh, J. S.; Flack, C. E.; Horswill, A. R. Peptide Signaling in the Staphylococci Chem. Rev. 2011, 111, 117-151 10.1021/cr100370n
250. Novick, R. P.; Geisinger, E. Quorum Sensing in Staphylococci Annu. Rev. Genet. 2008, 42, 541-564 10.1146/annurev.genet.42.110807.091640
251. Gripenland, J.; Netterling, S.; Loh, E.; Tiensuu, T.; Toledo-Arana, A.; Johansson, J. RNAs: Regulators of Bacterial Virulence Nat. Rev. Microbiol. 2010, 8, 857-866 10.1038/nrmicro2457
252. Mayville, P.; Ji, G.; Beavis, R.; Yang, H.; Goger, M.; Novick, R. P.; Muir, T. W. Structure-Activity Analysis of Synthetic Autoinducing Thiolactone Peptides from Staphylococcus aureus Responsible for Virulence Proc. Natl. Acad. Sci. U. S. A. 1999, 96, 1218-1223 10.1073/pnas.96.4.1218
253. Wright, J. S.; Lyon, G. J.; George, E. a; Muir, T. W.; Novick, R. P. Hydrophobic Interactions Drive Ligand-Receptor Recognition for Activation and Inhibition of Staphylococcal Quorum Sensing Proc. Natl. Acad. Sci. U. S. A. 2004, 101, 16168-16173 10.1073/pnas.0404039101
254. George, E. A.; Muir, T. W. Molecular Mechanisms of Agr Quorum Sensing in Virulent ChemBioChem 2007, 8, 847-855 10.1002/cbic.200700023
255. Wang, B.; Muir, T. W. Regulation of Virulence in Staphylococcus aureus: Molecular Mechanisms and Remaining Puzzles Cell Chem. Biol. 2016, 23, 214-224 10.1016/j.chembiol.2016.01.004
256. Tal-Gan, Y.; Stacy, D. M.; Foegen, M. K.; Koenig, D. W.; Blackwell, H. E. Highly Potent Inhibitors of Quorum Sensing in Staphylococcus aureus Revealed Through a Systematic Synthetic Study of the Group-III Autoinducing Peptide J. Am. Chem. Soc. 2013, 135, 7869-7882 10.1021/ja3112115
257. Tal-Gan, Y.; Ivancic, M.; Cornilescu, G.; Cornilescu, C. C.; Blackwell, H. E. Structural Characterization of Native Autoinducing Peptides and Abiotic Analogues Reveals Key Features Essential for Activation and Inhibition of an AgrC Quorum Sensing Receptor in Staphylococcus aureus J. Am. Chem. Soc. 2013, 135, 18436-18444 10.1021/ja407533e
258. Tal-Gan, Y.; Ivancic, M.; Cornilescu, G.; Yang, T.; Blackwell, H. E. Highly Stable, Amide-Bridged Autoinducing Peptide Analogues That Strongly Inhibit the AgrC Quorum Sensing Receptor in Staphylococcus aureus Angew. Chem., Int. Ed. 2016, 55, 8913-8917 10.1002/anie.201602974
259. Vasquez, J. K.; Tal-Gan, Y.; Cornilescu, G.; Tyler, K. A.; Blackwell, H. E. Simplified AIP-II Peptidomimetics Are Potent Inhibitors of Staphylococcus aureus AgrC Quorum Sensing Receptors ChemBioChem 2017, 18, 413-423 10.1002/cbic.201600516
260. Yang, T.; Tal-Gan, Y.; Paharik, A. E.; Horswill, A. R.; Blackwell, H. E. Structure-Function Analyses of a Staphylococcus epidermidis Autoinducing Peptide Reveals Motifs Critical for AgrC-Type Receptor Modulation ACS Chem. Biol. 2016, 11, 1982-1991 10.1021/acschembio.6b00120
261. Blaser, M. J. Antibiotic Use and Its Consequences for the Normal Microbiome Science 2016, 352, 544-545 10.1126/science.aad9358
262. Cho, I.; Blaser, M. J. The Human Microbiome: At the Interface of Health and Disease Nat. Rev. Genet. 2012, 13, 260-270 10.1038/nrg3182
263. Blaser, M. Stop the Killing of Beneficial Bacteria Nature 2011, 476, 393-394 10.1038/476393a
264. Hicks, L. A.; Blaser, M. J. Variability in Antibiotic Prescribing: An Inconvenient Truth J. Pediatric Infect. Dis. Soc. 2015, 4, e136-e138 10.1093/jpids/piu106
265. Cox, L. M.; Yamanishi, S.; Sohn, J.; Alekseyenko, A. V.; Leung, J. M.; Cho, I.; Kim, S. G.; Li, H.; Gao, Z.; Mahana, D. et al. Altering the Intestinal Microbiota during a Critical Developmental Window Has Lasting Metabolic Consequences Cell 2014, 158, 705-721 10.1016/j.cell.2014.05.052
266. Hill, C.; Jain, A.; Takemoto, H.; Silver, M. D.; Nagesh, S. V. S.; Ionita, C. N.; Bednarek, D. R.; Rudin, S. Antibiotics in Early Life and Obesity Nat. Rev. Endocrinol. 2015, 73, 389-400
267. Bokulich, N. A.; Chung, J.; Battaglia, T.; Henderson, N.; Jay, M.; Li, H.; A, D. L.; Wu, F.; Perez-Perez, G. I.; Chen, Y. et al. Antibiotics, Birth Mode, and Diet Shape Microbiome Maturation during Early Life Sci. Transl. Med. 2016, 8, 1-13 10.1126/scitranslmed.aad7121
268. Parenti, F.; Pagani, H.; Beretta, G. Lipiarmycin, a New Antibiotic from Actinoplanes I. Description of the Producer Strain and Fermentation Studies J. Antibiot. 1975, 28, 247-252 10.7164/antibiotics.28.247
269. Coronelli, C.; White, R. J.; Lancini, G. C.; Parenti, F. Lipiarmycin, a New Antibiotic from Actinoplanes. II. Isolation, Chemical, Biological and Biochemical Characterization J. Antibiot. 1975, 28, 253-259 10.7164/antibiotics.28.253
270. Sergio, S.; Pirali, G.; White, R.; Parenti, F. Lipiarmycin, a New Antibiotic from Actinoplanes. III. Mechanism of Action J. Antibiot. 1975, 28, 543-549 10.7164/antibiotics.28.543
271. Cavalleri, B.; Arnone, A.; Di Modugno, E.; Nasini, G.; Goldstein, B. P. Structure and Biological Activity of Lipiarmycin B J. Antibiot. 1988, 41, 308-315 10.7164/antibiotics.41.308
272. Hochlowski, J. E.; Swanson, S. J.; Ranfranz, L. M.; Whittern, D. N.; Buko, A. M.; McAlpine, J. B. Tiacumicins, a Novel Complex of 18-Membered Macrolides. II. Isolation and Structure Determination J. Antibiot. 1987, 40, 575-588 10.7164/antibiotics.40.575
273. Swanson, R. N.; Hardy, D. J.; Shipkowitz, N. L.; Hanson, C. W.; Ramer, N. C.; Fernandes, P. B.; Clement, J. J. In Vitro and In Vivo Evaluation of Tiacumicins B and C against Clostridium difficile Antimicrob. Agents Chemother. 1991, 35, 1108-1111 10.1128/AAC.35.6.1108
274. Cornely, O. A.; Crook, D. W.; Esposito, R.; Poirier, A.; Somero, M. S.; Weiss, K.; Sears, P.; Gorbach, S. Fidaxomicin versus Vancomycin for Infection with Clostridium difficile in Europe, Canada, and the USA: A Double-Blind, Non-Inferiority, Randomised Controlled Trial Lancet Infect. Dis. 2012, 12, 281-289 10.1016/S1473-3099(11)70374-7
275. Louie, T. J.; Miller, M. A.; Mullane, K. M.; Weiss, K.; Lentnek, A.; Golan, Y.; Gorbach, S.; Sears, P.; Shue, Y.-K. Fidaxomicin versus Vancomycin for Clostridium difficile Infection N. Engl. J. Med. 2011, 364, 422-431 10.1056/NEJMoa0910812
276. Erb, W.; Grassot, J. M.; Linder, D.; Neuville, L.; Zhu, J. Enantioselective Synthesis of Putative Lipiarmycin Aglycon Related to Fidaxomicin/tiacumicin B Angew. Chem., Int. Ed. 2015, 54, 1929-1932 10.1002/anie.201409475
277. Glaus, F.; Altmann, K. H. Total Synthesis of the Tiacumicin B (Lipiarmycin A3/fidaxomicin) Aglycone Angew. Chem., Int. Ed. 2015, 54, 1937-1940 10.1002/anie.201409510
278. Miyatake-Ondozabal, H.; Kaufmann, E.; Gademann, K. Total Synthesis of the Protected Aglycon of Fidaxomicin (Tiacumicin B, Lipiarmycin A3) Angew. Chem., Int. Ed. 2015, 54, 1933-1936 10.1002/anie.201409464
279. Kaufmann, E.; Hattori, H.; Miyatake-Ondozabal, H.; Gademann, K. Total Synthesis of the Glycosylated Macrolide Antibiotic Fidaxomicin Org. Lett. 2015, 17, 3514-3517 10.1021/acs.orglett.5b01602
280. Xiao, Y.; Li, S.; Niu, S.; Ma, L.; Zhang, G.; Zhang, H.; Zhang, G.; Ju, J.; Zhang, C. Characterization of Tiacumicin B Biosynthetic Gene Cluster Affording Diversified Tiacumicin Analogues and Revealing a Tailoring Dihalogenase J. Am. Chem. Soc. 2011, 133, 1092-1105 10.1021/ja109445q
281. Li, W.; Estrada-de los Santos, P.; Matthijs, S.; Xie, G.-L.; Busson, R.; Cornelis, P.; Rozenski, J.; De Mot, R. Promysalin, a Salicylate-Containing Pseudomonas putida Antibiotic, Promotes Surface Colonization and Selectively Targets Other Pseudomonas Chem. Biol. 2011, 18, 1320-1330 10.1016/j.chembiol.2011.08.006
282. Steele, A. D.; Knouse, K. W.; Keohane, C. E.; Wuest, W. M. Total Synthesis and Biological Investigation of (-)-Promysalin J. Am. Chem. Soc. 2015, 137, 7314-7317 10.1021/jacs.5b04767
283. Kaduskar, R. D.; Dhavan, A. A.; Dallavalle, S.; Scaglioni, L.; Musso, L. Total Synthesis of the Salicyldehydroproline-Containing Antibiotic Promysalin Tetrahedron 2016, 72, 2034-2041 10.1016/j.tet.2016.03.009
284. Steele, A. D.; Keohane, C. E.; Knouse, K. W.; Rossiter, S. E.; Williams, S. J.; Wuest, W. M. Diverted Total Synthesis of Promysalin Analogs Demonstrates That an Iron-Binding Motif Is Responsible for Its Narrow-Spectrum Antibacterial Activity J. Am. Chem. Soc. 2016, 138, 5833-5836 10.1021/jacs.6b03373
285. Knouse, K. W.; Wuest, W. M. The Enantioselective Synthesis and Biological Evaluation of Chimeric Promysalin Analogs Facilitated by Diverted Total Synthesis J. Antibiot. 2016, 69, 337-339 10.1038/ja.2016.4
286. Jansen, R.; Irschik, H.; Huch, V.; Schummer, D.; Steinmetz, H.; Bock, M.; Schmidt, T.; Kirschning, A.; Müller, R. Carolacton-A Macrolide Ketocarbonic Acid That Reduces Biofilm Formation by the Caries- and Endocarditis-Associated Bacterium Streptococcus mutans Eur. J. Org. Chem. 2010, 2010, 1284-1289 10.1002/ejoc.200901126
287. Reck, M.; Rutz, K.; Kunze, B.; Tomasch, J.; Surapaneni, S. K.; Schulz, S.; Wagner-Döbler, I. The Biofilm Inhibitor Carolacton Disturbs Membrane Integrity and Cell Division of Streptococcus mutans through the Serine/Threonine Protein Kinase PknB J. Bacteriol. 2011, 193, 5692-5706 10.1128/JB.05424-11
288. Donner, J.; Reck, M.; Bergmann, S.; Kirschning, A.; Müller, R.; Wagner-Döbler, I. The Biofilm Inhibitor Carolacton Inhibits Planktonic Growth of Virulent Pneumococci via a Conserved Target Sci. Rep. 2016, 6, 29677 10.1038/srep29677
289. Schmidt, T.; Kirschning, A. Total Synthesis of Carolacton, a Highly Potent Biofilm Inhibitor Angew. Chem., Int. Ed. 2012, 51, 1063-1066 10.1002/anie.201106762
290. Stumpp, N.; Premnath, P.; Schmidt, T.; Ammermann, J.; Dräger, G.; Reck, M.; Jansen, R.; Stiesch, M.; Wagner-Döbler, I.; Kirschning, A. Synthesis of New Carolacton Derivatives and their Activity Against Biofilms of Oral Bacteria Org. Biomol. Chem. 2015, 13, 5765-5774 10.1039/C5OB00460H
291. Hallside, M. S.; Brzozowski, R. S.; Wuest, W. M.; Phillips, A. J. A Concise Synthesis of Carolacton Org. Lett. 2014, 16, 1148-1151 10.1021/ol500004k
292. Solinski, A. E.; Koval, A. B.; Brzozowski, R. S.; Morrison, K. R.; Carson, C. E.; Eshraghi, A. R.; Zhou, G.; Quivey, R. G.; Voelz, V. A.; Buttaro, B. A. et al. The Diverted Total Synthesis of Carolacton-Inspired Analogs Yields Three Distinct Phenotypes in Streptococcus mutans Biofilms J. Am. Chem. Soc. 2017, 139, 7188-7191 10.1021/jacs.7b03879
293. Kuilya, T. K.; Goswami, R. K. Stereoselective Total Synthesis of Carolacton Org. Lett. 2017, 19, 2366-2369 10.1021/acs.orglett.7b00903
294. Huigens, R. W., III; Ma, L.; Gambino, C.; Moeller, P. D. R.; Basso, A.; Cavanagh, J.; Wozniak, D. J.; Melander, C. Control of Bacterial Biofilms with Marine Alkaloid Derivatives Mol. BioSyst. 2008, 4, 614-621 10.1039/b719989a
295. Huigens, R. W.; Richards, J. J.; Parise, G.; Ballard, T. E.; Zeng, W.; Deora, R.; Melander, C. Inhibition of Pseudomonas aeruginosa Biofilm Formation with Bromoageliferin Analogues J. Am. Chem. Soc. 2007, 129, 6966-6967 10.1021/ja069017t
296. Richards, J. J.; Ballard, T. E.; Huigens, R. W.; Melander, C. Synthesis and Screening of an Oroidin Library against Pseudomonas aeruginosa Biofilms ChemBioChem 2008, 9, 1267-1279 10.1002/cbic.200700774
297. Lindsey, E. A.; Brackett, C. M.; Mullikin, T.; Alcaraz, C.; Melander, C. The Discovery of N-1 Substituted 2-Aminobenzimidazoles as Zinc-Dependent S. Aureus Biofilm Inhibitors MedChemComm 2012, 3, 1462 10.1039/c2md20244a
298. Nguyen, T. V.; Blackledge, M. S.; Lindsey, E. A.; Minrovic, B. M.; Ackart, D. F.; Jeon, A. B.; Obregon-Henao, A.; Melander, R. J.; Basaraba, R. J.; Melander, C. The Discovery of 2-Aminobenzimidazoles That Sensitize Mycobacterium smegmatis and M. tuberculosis to β-Lactam Antibiotics in a Pattern Distinct from SS-Lactamase Inhibitors Angew. Chem., Int. Ed. 2017, 56, 3940-3944 10.1002/anie.201612006
299. Pettersen, E. F.; Goddard, T. D.; Huang, C. C.; Couch, G. S.; Greenblatt, D. M.; Meng, E. C.; Ferrin, T. E. UCSF Chimera - a visualization system for exploratory research and analysis J. Comput. Chem. 2004, 25, 1605-1612 10.1002/jcc.20084