Influence of 4′-O-Glycoside Constitution and Configuration on Ribosomal Selectivity of Paromomycin

Journal of the American Chemical Society

Volumn 137, Issue 24, 2015, Pages 7706-7717

  Matsushita, Takahiko ^a   Chen, Weiwei ^a   Juskeviciene, Reda ^b   Teo, Youjin ^b   Shcherbakov, Dimitri ^b   Vasella, Andrea ^c   Böttger, Erik C ^b   Crich, David ^a  

^a WAYNE STATE UNIVERSITY   (United States)

^b UNIVERSITY OF ZURICH   (Switzerland)

^c ETH ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

BACTERIA; BIOSYNTHESIS; ESCHERICHIA COLI; SUGARS;

AMINOGLYCOSIDE ANTIBIOTICS; ANTI-BACTERIAL ACTIVITY; ENTEROBACTER CLOACAE; KLEBSIELLA PNEUMONIA; METHICILLIN-RESISTANT STAPHYLOCOCCUS AUREUS; MITOCHONDRIAL RIBOSOMES; SPECIFIC RESISTANCES; SYSTEMIC TOXICITIES;

MACROMOLECULES;

2 DEOXY BETA DEXTRO XYLOPYRANOSYL PAROMOMYCIN; 4' 2 (2 HYDROXY ETHYL) PAROMOMYCIN; 4' 2 ETHYL PAROMOMYCIN; 4' 2 PROPYL PAROMOMYCIN; ALPHA DEXTRO AIBOFURANOSYL PAROMOMYCIN; ALPHA DEXTRO ARABINOFURANOSYL PAROMOMYCIN; ALPHA DEXTRO ARABINOPYRANOSYL PAROMOMYCIN; ALPHA DEXTRO GALACTOPYRANOSYL PAROMOMYCIN; ALPHA DEXTRO GLUCOPYRANOSYL PAROMOMYCIN; ALPHA DEXTRO MANNOPYRANOSYL PAROMOMYCIN; ALPHA DEXTRO RIBOFURANOSYL PAROMOMYCIN; ALPHA DEXTRO XYLOPYRANOSYL PAROMOMYCIN; ALPHA LEVO ARABINOPYRANOSYL PAROMOMYCIN; ALPHA LEVO XYLOPYRANOSYL PAROMOMYCIN; AMINOGLYCOSIDE ANTIBIOTIC AGENT; APRAMYCIN; BETA DEXTRO ARABINOPYRANOSYL PAROMOMYCIN; BETA DEXTRO GALACTOPYRANOSYL PAROMOMYCIN; BETA DEXTRO GLUCOPYRANOSYL PAROMOMYCIN; BETA DEXTRO MANNOPYRANOSYL PAROMOMYCIN; BETA DEXTRO RABINOFURANOSYL PAROMOMYCIN; BETA DEXTRO RIBOFURANOSYL PAROMOMYCIN; BETA DEXTRO RIBOPYRANOSYL PAROMOMYCIN; BETA DEXTRO XYLOPYRANOSYL PAROMOMYCIN; BETA LEVO ARABINOPYRANOSYL PAROMOMYCIN; BETA LEVO XYLOPYRANOSYL PAROMOMYCIN; PAROMOMYCIN; RIBOSOME RNA; UNCLASSIFIED DRUG; ANTIINFECTIVE AGENT;

ACINETOBACTER BAUMANNII; ALLELE; ANTIBACTERIAL ACTIVITY; ARTICLE; BACTERIUM ISOLATE; BINDING AFFINITY; CONTROLLED STUDY; DRUG SELECTIVITY; DRUG SYNTHESIS; ENANTIOMER; ENTEROBACTER CLOACAE; ESCHERICHIA COLI; GLYCOSYLATION; HYDROGENOLYSIS; KLEBSIELLA PNEUMONIAE; METHICILLIN RESISTANT STAPHYLOCOCCUS AUREUS; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; OTOTOXICITY; PROTEIN SYNTHESIS; PSEUDOMONAS AERUGINOSA; RIBOSOME; RNA TRANSLATION; STAUDINGER REACTION; ANALOGS AND DERIVATIVES; BACTERIAL INFECTIONS; BACTERIUM; CHEMISTRY; CONFORMATION; CYTOLOGY; DRUG EFFECTS; HUMAN;

ANTI-BACTERIAL AGENTS; BACTERIA; BACTERIAL INFECTIONS; HUMANS; MOLECULAR CONFORMATION; PAROMOMYCIN; RIBOSOMES;

EID: 84932623465     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.5b02248     Document Type: Article

References (117)

1. Holdren, J. P.; Lander, E. S. Report to the President on Combatting Antibiotic Resistance; President's Council of Advisors on Science and Technology, Washington DC, Sept 2014.
2. Payne, D. J.; Gwynn, M. N.; Holmes, D. J.; Pompliano, D. L. Nat. Rev.: Drug Discovery 2007, 6, 29-40
3. French, G. L. Int. J. Antimicrob. Agents 2010, 36 (Suppl 3) S3-S7
4. Walsh, C. T. Chem. Rev. 2009, 105, 391-744
5. Karaiskos, I.; Giamarellou, H. Exp. Opin. Pharmacother. 2015, 15, 1351-1370
6. Wright, P. M.; Seiple, I. B.; Myers, A. G. Angew. Chem., Int. Ed. 2014, 53, 8840-8863
7. Nicolaou, K. C. Angew. Chem., Int. Ed. 2014, 53, 9128-9140
8. Li, J. W.-H.; Vederas, J. C. Science 2009, 325, 161-165
9. Wright, G. D.; Sutherland, A. D. Trends Mol. Med. 2007, 13, 260-267
10. Butler, M. S.; Buss, A. D. Biochem. Pharmacol. 2006, 71, 919-929
11. Walsh, C. T.; Fischbach, M. A. J. Am. Chem. Soc. 2010, 132, 2469-2493
12. Newman, D. J.; Cragg, G. M. J. Nat. Prod. 2007, 70, 461-477
13. Connell, K. M. G. O.; Hodgkinson, J. T.; Sore, H. F.; Welch, M.; Salmond, G. P. C.; Spring, D. R. Angew. Chem., Int. Ed. 2013, 52, 10706-10733
14. Aminoglycoisde Antibiotics: From Chemical Biology to Drug Discovery; Arya, D. P., Ed.; Wiley: Hoboken, NJ, 2007.
15. Haddad, J.; Kotra, L. P.; Mobashery, S. In Glycochemsitry: Principles, Synthesis, and Applications; Wang, P. G.; Bertozzi, C. R., Eds.; Dekker: New York, 2001; pp 307-351.
16. Armstrong, E. S.; Kostrub, C. F.; Cass, R. T.; Moser, H. E.; Serio, A. W.; Miller, G. H. In Antibiotic Discovery and Development; Dougherty, T. J.; Pucci, M. J., Eds.; Springer Science+Business Media: Berlin, 2012; pp 229-269.
17. Becker, B.; Cooper, M. A. ACS Chem. Biol. 2013, 8, 105-115
18. Poulikakos, P.; Falagas, M. E. Exp. Opin. Pharmacother. 2013, 14, 1585-1597
19. Vakulenko, S. B.; Mobashery, S. Clin. Microbiol. Rev. 2003, 16, 430-450
20. Jackson, J.; Chen, C.; Buising, K. Curr. Opin. Infect. Dis. 2013, 26, 516-525
21. Fosso, M. Y.; Li, Y.; Garneau-Tsodikova, S. Med. Chem. Commun. 2014, 5, 1075-1091
22. Critically Important Antimicrobials for Human Medicine: Categorization for the Development of Risk Management Strategies to contain Antimicrobial Resistance due to Non-Human Antimicrobial Use, Report of the Second WHO Expert Meeting, Copenhagen, May 29-31, 2007; WHO: Geneva, Switzerland, 2007.
23. Chambers, H. F. In Goodman and Gilman's The Pharmaceutical Basis of Therapeutics; 10 th ed.; Hardman, J. G.; Limbird, L. E., Eds.; McGraw-Hill: New York, 1996; pp 1103-1121.
24. Hanberger, H.; Edlund, C.; Furebring, M.; Giske, C. G.; Melhus, A.; Nilsson, L. E.; Petersson, J.; Sjölin, J.; Ternhag, A.; Werner, M.; Eliasson, E. Scand. J. Infect. Dis. 2013, 45, 161-175
25. Carter, A. P.; Clemons, W. M.; Brodersen, D. E.; Morgan-Warren, R. J.; Wimberly, B. T.; Ramakrishnan, V. Nature 2000, 407, 340-348
26. Garreau de Loubresse, N.; Prokhorova, I.; Holtkamp, W.; Rodnina, M. V.; Yusupova, G.; Yusupov, M. Nature 2014, 513, 517-523
27. François, B.; Russell, R. J. M.; Murray, J. B.; Aboul-ela, F.; Masquid, B.; Vicens, Q.; Westhof, E. Nucleic Acids Res. 2005, 33, 5677-5690
28. Peske, F.; Savelsbergh, A.; Katunin, V. I.; Rodnina, M. V.; Wintermeyer, W. J. Mol. Biol. 2004, 343, 1183-1194
29. Feldman, M. B.; Terry, D. S.; Altman, R. B.; Blanchard, S. C. Nat. Chem. Biol. 2010, 6, 54-62
30. Moazed, D.; Noller, H. F. Nature 1987, 327, 389-394
31. Tsai, A.; Uemura, S.; Johansson, M.; Puglisi, E. V.; Marshall, R. A.; Echeverría Aitken, C.; Korlach, J.; Ehrenberg, M.; Puglisi, J. D. Cell Rep. 2013, 3, 497-508
32. Marshall, R. A.; Puglisi, J. D. In Aminoglycoside Antibiotics: From Chemical Biology to Drug Discovery; Ayra, D. P., Ed.; Wiley: Hoboken, NJ, 2007; pp 181-207.
33. Kondo, J.; Westhof, E. In Antibioitcs: Targets, Mechanisms and Resistance; Gualerzi, C. O.; Brandi, L.; Fabbretti, A.; Pon, C. L., Eds.; Wiley-VCH: Weinheim, 2014; pp 453-470.
34. Weizman, H.; Tor, Y. In Carbohydrate-Based Drug Discovery; Wong, C.-H., Ed.; Wiley-VCH: Weinheim, 2003; Vol. 2, pp 661-683.
35. Magnet, S.; Blanchard, J. S. Chem. Rev. 2005, 105, 477-497
36. Houghton, J. L.; Green, K. D.; Chen, W.; Garneau-Tsodikova, S. ChemBioChem 2010, 11, 880-902
37. Ramirez, M. S.; Tolmasky, M. E. Drug Resist. Updates 2010, 13, 151-171
38. Labby, K. J.; Garneau-Tsodikova, S. Fut. Med. Chem. 2013, 5, 1285-1309
39. Yang, L.; Ye, X. S. Curr. Top. Med. Chem. 2010, 10, 1898-1926
40. Umezawa, S. Adv. Carbohydr. Chem. Biochem. 1974, 30, 111-182
41. Haddad, J.; Liu, M.-Z.; Mobashery, S. In Glycochemistry: Principles, Synthesis, and Applications; Wang, P. G.; Bertozzi, C. R., Eds.; Dekker: New York, 2001; pp 353-424.
42. Wang, J.; Chang, C.-W. T. In Aminoglycoside Antibiotics; Arya, D. P., Ed.; Wiley: Hoboken, NJ, 2007; pp 141-180.
43. Berkov-Zrihen, Y.; Fridman, M. In Modern Synthetic Methods in Carbohydrate Chemistry; From Monosaccharides to Complex Glycoconjugates; Werz, D. B.; Vidal, S., Eds.; Wiley: Weinheim, 2014; pp 161-190.
44. Aggen, J. B.; Armstrong, E. S.; Goldblum, A. A.; Dozzo, P.; Linsell, M. S.; Gliedt, M. J.; Hildebrandt, D. J.; Feeney, L. A.; Kubo, A.; Matias, R. D.; Lopez, S.; Gomez, M.; Wlasichuk, K. B.; Diokno, R.; Miller, G. H.; Moser, H. E. Antimicrob. Agents Chemother. 2010, 54, 4636-4642
45. Zhanel, G. G.; Lawson, C. D.; Zelenitsky, S.; Findlay, B.; Schweizer, F.; Adam, H.; Walkty, A.; Rubinstein, E.; Gin, A. S.; Hoban, D. J.; Lynch, J. P.; Karlowsky, J. A. Exp. Rev. Anti-infect. Ther. 2012, 10, 459-473
46. Hanessian, S.; Maianti, J. P.; Matias, R. D.; Feeney, L. A.; Armstrong, E. S. Org. Lett. 2011, 13, 6476-6479
47. Maianti, J. P.; Kanazawa, H.; Dozzo, P.; Matias, R. D.; Feeney, L. A.; Armstrong, E. S.; Hildebrandt, D. J.; Kane, T. R.; Gliedt, M. J.; Goldblum; Linsell, M. S.; Aggen, J. B.; Kondo, J.; Hanessian, S. ACS Chem. Biol. 2014, 9, 2067-2073
48. Mingeot-Leclercq, M.-P.; Tulkens, P. M. Antimicrob. Agents Chemother. 1999, 43, 1003-1012
49. Avent, M. L.; Rogers, B. A.; Cheng, A. C.; Paterson, D. L. Int. Med. 2011, 41, 441-449
50. Duggal, P.; Sarkar, M. BMC Ear Nose Throat Disord. 2007, 10.1186/1472-6815-7-5
51. Peloquin, C. A.; Berning, S. E.; Nitta, A. T.; Simone, P. M.; Goble, M.; Huitt, G. A.; Iseman, M. D.; Cook, J. L.; Curran-Everett, D. Clin. Infect. Dis. 2004, 38, 1538-1544
52. Prezant, T. R.; Agapian, J. V.; Bohlman, M. C.; Bu, X.; Öztas, S.; Qiu, W.-Q.; Arnos, K. S.; Cortopassi, G. A.; Jaber, L.; Rotter, J. I.; Shohat, M.; Fischel-Ghodsian, N. Nat. Genet. 1993, 4, 289-294
53. Böttger, E. C.; Schacht, J. Hearing Res. 2013, 303, 12-19
54. Hobbie, S. N.; Akshay, S.; Kalapala, S. K.; Bruell, C.; Shcherbakov, D.; Böttger, E. C. Proc. Natl. Acad. Sci. U.S.A. 2008, 105, 20888-20893
55. Hobbie, S. N.; Bruell, C. M.; Akshay, S.; Kalapala, S. K.; Shcherbakov, D.; Böttger, E. C. Proc. Natl. Acad. Sci. U.S.A. 2008, 105, 3244-3249
56. Hobbie, S. N.; Kalapala, S. K.; Akshay, S.; Bruell, C.; Schmidt, S.; Dabow, S.; Vasella, A.; Sander, P.; Böttger, E. C. Nucleic Acids Res. 2007, 35, 6086-6093
57. Francis, S. P.; Katz, J.; Fanning, K. D.; Harris, K. A.; Nicholas, B. D.; Lacy, M.; Pagana, J.; Agris, P. F.; Shin, J.-B. J. Neurosci. 2013, 33, 3079-3093
58. Shulman, E.; Belakhov, V.; Wei, G.; Kendall, A.; Meyron-Holtz, E. G.; Ben-Shachar, D.; Schacht, J.; Baasov, T. J. Biol. Chem. 2014, 289, 2318-2330
59. Henley, C. M.; Schacht, J. Audiology 1988, 27, 137-146
60. Dulon, D.; Aran, J. M.; Zajic, G.; Schacht, J. Antimicrob. Agents Chemother. 1986, 30, 96-100
61. Aran, J. M.; Chappert, C.; Dulon, D.; Erre, J. P.; Aurousseau, C. Hearing Res. 1995, 82, 179-183
62. Matt, T.; Ng, C. L.; Lang, K.; Sha, S.-H.; Akbergenov, R.; Shcherbakov, D.; Meyer, M.; Duscha, S.; Xie, J.; Dubbaka, S. R.; Perez-Fernandez, D.; Vasella, A.; Ramakrishnan, V.; Schacht, J.; Böttger, E. C. Proc. Natl. Acad. Sci. U.S.A. 2012, 109, 10984-10989
63. Meyer, M.; Freihofer, P.; Scherman, M.; Teague, J.; Lenaerts, A.; Böttger, E. C. Antimicrob. Agents Chemother. 2014, 54, 6938-6941
64. Perez-Fernandez, D.; Shcherbakov, D.; Matt, T.; Leong, N. C.; Kudyba, I.; Duscha, S.; Boukari, H.; Patak, R.; Dubbaka, S. R.; Lang, K.; Meyer, M.; Akbergenov, R.; Freihofer, P.; Vaddi, S.; Thommes, P.; Ramakrishnan, V.; Vasella, A.; Böttger, E. C. Nature Commun. 2014, 10.1038/ncomms4112
65. Duscha, S.; Boukari, H.; Shcherbakov, D.; Salian, S.; Silva, S.; Kendall, A.; Kato, T.; Akbergenov, R.; Perez-Fernandez, D.; Bernet, B.; Vaddi, S.; Thommes, P.; Schacht, J.; Crich, D.; Vasella, A.; Böttger, E. C. mBio 5 ((5): e01827-14 10.1128/mBio.01827-14.
66. Mandhapati, A. R.; Shcherbakov, D.; Duscha, S.; Vasella, A.; Böttger, E. C.; Crich, D. ChemMedChem 2014, 9, 2074-2083
67. Chen, W.; Matsushita, T.; Shcherbakov, D.; Boukari, H.; Vasella, A.; Böttger, E. C.; Crich, D. MedChemComm 2014, 5, 1179-1187
68. Pathak, R.; Perez-Fernandez, D.; Nandurdikar, R.; Kalapala, S. K.; Böttger, E. C.; Vasella, A. Helv. Chim. Acta 2008, 91, 1533-1552
69. Qiu, D.; Schmidt, R. R. Synthesis 1990, 875-877
70. Hada, N.; Miyamura, A.; Ohtsuka, I.; Kiuchi, F. Heterocycles 2014, 88, 689-704
71. Zhao, G.-L.; Yu, Z.-Y.; Li, Y.; Pang, L.-N.; Wang, J.-W. Chin. J. Chem. 2008, 26, 158-164
72. Sato, T.; Fujita, Y.; Otera, J.; Nozaki, H. Tetrahedron Lett. 1992, 33, 239-242
73. Kametani, T.; Kawamura, K.; Honda, T. J. Am. Chem. Soc. 1987, 109, 3010-3017
74. Touisni, N.; Maresca, A.; McDonald, P. C.; Lou, Y.; Scozzafava, A.; Dedhar, S.; Winum, J.-y.; Supuran, C. T. J. Med. Chem. 2011, 54, 8271-8277
75. Chiu-Machado, I.; Castro-Palomino, J. C.; Madrazo-Alonso, O.; Loipetegui-Palacios, C.; Verez-Bencomo, V. J. Carbohydr. Chem. 1995, 14, 551-561
76. Lafont, D.; Descotes, G. Carbohydr. Res. 1987, 166, 195-209
77. Costantino, V.; Imperatore, C.; Fattorusso, E.; Mangoni, A. Tetrahedron Lett. 2000, 41, 9177-9180
78. Codée, J. D. C.; van den Bos, L. J.; Litjens, R. E. J. N.; Overkleeft, H. S.; van Boeckel, C. A. A.; van Boom, J. H.; van der Marel, G. A. Tetrahedron 2004, 60, 1057-1064
79. Crich, D.; Smith, M.; Yao, Q.; Picione, J. Synthesis 2001, 323-326
80. Konradsson, P.; Mootoo, D. R.; McDevitt, R. E.; Fraser-Reid, B. J. Chem. Soc., Chem. Commun. 1990, 270-272
81. Konradsson, P.; Udodong, U. E.; Fraser-Reid, B. Tetrahedron Lett. 1990, 31, 4313-4316
82. Schmidt, R. R. Angew. Chem., Int. Ed. 1986, 25, 212-235
83. Issa, J. P.; Lloyd, D.; Steliotes, E.; Bennett, C. S. Org. Lett. 2013, 15, 4170-4173
84. Issa, J. P.; Bennett, C. S. J. Am. Chem. Soc. 2014, 136, 5740-5744
85. McNaught, A. D. Carbohydr. Res. 1997, 297, 1-92
86. Abe, Y.; Nakagawa, S.; Naito, T.; Kawaguchi, H. J. Antibiot. 1981, 34, 1434-1446
87. Chang, C.-W. T.; Hui, Y.; Elchert, B.; Wang, J.; Li, J.; Rai, R. Org. Lett. 2002, 4, 4603-4606
88. Wang, J.; Li, J.; Tuttle, D.; Takemoto, J. Y.; Chang, C.-W. T. Org. Lett. 2002, 4, 3997-4000
89. Fridman, M.; Belakhov, V.; Yaron, S.; Baasov, T. Org. Lett. 2003, 5, 3575-3578
90. Seeberger, P. H.; Baumann, M.; Zhang, G.; Kanemitsu, T.; Swayze, E. E.; Hofstadler, S. A.; Griffey, R. H. Synlett 2003, 1323-1326
91. Elchert, B.; Li, J.; Wang, J.; Hui, Y.; Rai, R.; Ptak, R.; Ward, P.; Takemoto, J. Y.; Bensaci, M.; Chang, C.-W. T. J. Org. Chem. 2004, 69, 1513-1523
92. Hainrichson, M.; Pokrovskaya, V.; Shallom-Shezifi, D.; Fridman, M.; Belakhov, V.; Shachar, D.; Yaron, S.; Baasov, T. Bioorg. Med. Chem. 2005, 13, 5797-5807
93. Wang, J.; Li, J.; Chen, H.-N.; Chang, H.; Tanifum, C. T.; Liu; Czyryca, P. G.; Chang, C.-W. T. J. Med. Chem. 2005, 48, 6271-6285
94. Revuelta, J.; Vacas, T.; Bastida, A.; Asensio, J. L. Chem.-Eur. J. 2010, 16, 2986-2991
95. Rao, V. S. R.; Qasba, P. K.; Balaji, P. V.; Chandrasekaran, R. Conformation of Carbohydrates; Harwood Academic Publishers: Amsterdam, 1998.
96. Grindley, T. B. In Glycoscience: Chemistry and Chemical Biology; Fraser-Reid, B.; Tatsuta, K.; Thiem, J., Eds.; Springer: Berlin, 2001; Vol. 1, pp 3-51.
97. Duus, J. O.; Gotfredsen, C. H.; Bock, K. Chem. Rev. 2000, 100, 4589-4614
98. Altona, C.; Sundaralingam, M. J. Am. Chem. Soc. 1972, 94, 8205-8212
99. Costantino, V.; Fattorusso, E.; Imperatore, C.; Mangoni, A. J. Org. Chem. 2008, 73, 6158-6165
100. Taha, H. A.; Castillo, N.; Sears, D. N.; Wasylishen, R. E.; Lowary, T. L.; Roy, P.-N. J. Chem. Theory Comput. 2010, 6, 212-222
101. Taha, H. A.; Roy, P.-N.; Lowary, T. L. J. Chem. Theory Comput. 2011, 7, 420-432
102. Houseknecht, J. B.; Lowary, T. L.; Hadad, C. M. J. Phys. Chem. A 2003, 107, 5763-5777
103. Taha, H. A.; Richards, M. R.; Lowary, T. L. Chem. Rev. 2013, 113, 1851-1876
104. Nahoum, V.; Spector, S.; Loll, P. Acta Crystallogr., Sect. D 2011, 67, 592
105. Chu, S. S. C.; Jeffrey, G. A. Acta Crystallogr., Sect. B 1968, 24, 830-838
106. Brown, C. J. J. Chem. Soc. A 1966, 927-932
107. Jacobson, R. A.; Wunderlich, J. A.; Lipscomb, W. N. Acta Crystallogr., Sect. B 1961, 24, 598-607
108. Ham, J. T.; Williams, D. G. Acta Crystallogr., Sect. B 1970, 26, 1373-1383
109. Bernet, B.; Vasella, A. Helv. Chim. Acta 2000, 83, 2055-2071
110. Bohner, T. V.; Verena, B.; Vasella, A. Helv. Chim. Acta 1999, 82, 198-228
111. Ogle, J. M.; Ramakrishnan, V. Annu. Rev. Biochem. 2005, 74, 129-177
112. Akbergenov, R.; Shcherbakov, D.; Matt, T.; Duscha, S.; Meyer, M.; Perez-Fernandez, D.; Pathak, R.; Harish, S.; Kudyba, I.; Dubbaka, S. R.; Silva, S.; Ruiz Ruiz, M.; Salian, S.; Vasella, A.; Böttger, E. C. In Ribosomes: Structure, Function, and Dynamics; Rodnina, M. V.; Wintermeyer, W.; Green, R., Eds.; Springer-Verlag: Vienna, 2011; pp 249-261.
113. Pfister, P.; Hobbie, S.; Vicens, Q.; Böttger, E. C.; Westhof, E. ChemBioChem 2003, 4, 1078-1088
114. Greber, B. J.; Bieri, P.; Leibundgut, M.; Leitner, A.; Aebersold, R.; Boehringer, D.; Ban, N. Science 2015, 348, 303-308
115. Amunts, A.; Brown, A. D.; Toots, J.; Scheres, S. H. W.; Ramakrishnan, V. Science 2015, 348, 95-98
116. Ida, T.; Okamoto, R.; Shimauchi, C.; Okubo, T.; Kuga, A.; Inoue, M. J. Clin. Microbiol. 2001, 39, 3115-3121
117. Yan, R.-B.; Yuan, M.; Wu, Y.; You, X.; Ye, X.-S. Bioorg. Med. Chem. 2011, 19, 30-40