Peptide chemistry

Organic Letters

Volumn 14, Issue 17, 2012, Pages 4297-4302

  Lubell, William D ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

PEPTIDE;

CHEMISTRY; EDITORIAL; METHODOLOGY; ORGANIC CHEMISTRY;

CHEMISTRY, ORGANIC; PEPTIDES;

EID: 84866011215     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol302276u     Document Type: Editorial

References (71)

1. Dheur, J.; Ollivier, N.; Vallin, A.; Melnyk, O. Synthesis of Peptide Alkylthioesters Using the Intramolecular N, S-Acyl Shift Properties of Bis(2-sulfanylethyl)amido Peptides J. Org. Chem. 2011, 76, 3194-3202
2. Zheng, J.-S.; Chang, H.-N.; Wang, F.-L.; Liu, L. Fmoc Synthesis of Peptide Thioesters without Post-Chain-Assembly Manipulation J. Am. Chem. Soc. 2011, 133, 11080-11083
3. Eom, K. D.; Tam, J. P. Acid-Catalyzed Tandem Thiol Switch for Preparing Peptide Thioesters from Mercaptoethyl Esters Org. Lett. 2011, 13, 2610-2613
4. Sharma, I.; Crich, D. Direct Fmoc-Chemistry-Based Solid-Phase Synthesis of Peptidyl Thioesters J. Org. Chem. 2011, 76, 6518-6524
5. Raz, R.; Rademann, J. Fmoc-Based Synthesis of Peptide Thioesters for Native Chemical Ligation Employing a tert -Butyl Thiol Linker Org. Lett. 2011, 13, 1606-1609
6. Siman, P.; Karthikeyan, S. V.; Brik, A. Native Chemical Ligation at Glutamine Org. Lett. 2012, 14, 1520-1523
7. Malins, L. R.; Payne, R. J. Synthesis and Utility of β-Selenol- Phenylalanine for Native Chemical Ligation-Deselenization Chemistry Org. Lett. 2012, 14, 3142-3145
8. Ding, H.; Shigenaga, A.; Sato, K.; Morishita, K.; Otaka, A. Dual Kinetically Controlled Native Chemical Ligation Using a Combination of Sulfanylproline and Sulfanylethylanilide Peptide Org. Lett. 2011, 13, 5588-5591
9. Townsend, S. D.; Tan, Z.; Dong, S.; Shang, S.; Brailsford, J. A.; Danishefsky, S. J. Advances in Proline Ligation J. Am. Chem. Soc. 2012, 134, 3912-3916
10. Jastrzabek, K. G.; Subiros-Funosas, R.; Albericio, F.; Kolesinska, B.; Kaminski, Z. J. 4-(4,6-Di[2,2,2-trifluoroethoxy]-1,3,5-triazin-2-yl)-4- methylmorpholinium Tetrafluoroborate. Triazine-Based Coupling Reagents Designed for Coupling Sterically Hindered Substrates J. Org. Chem. 2011, 76, 4506-4513
11. Pinsker, A.; Einsiedel, J.; Harterich, S.; Waibel, R.; Gmeiner, P. A Highly Efficient Type I β-Turn Mimetic Simulating an Asx-Pro-Turn-Like Structure Org. Lett. 2011, 13, 3502-3505
12. Khan, S. N.; Kim, A.; Grubbs, R. H.; Kwon, Y.-U. Ring-Closing Metathesis Approaches for the Solid-Phase Synthesis of Cyclic Peptoids Org. Lett. 2011, 13, 1582-1585
13. Kong, J.; Chen, C.-yi; Balsells-Padros, J.; Cao, Y.; Dunn, R. F.; Dolman, S. J.; Janey, J.; Li, H.; Zacuto, M. J. Synthesis of the HCV Protease Inhibitor Vaniprevir (MK-7009) Using Ring-Closing Metathesis Strategy J. Org. Chem. 2012, 77, 3820-3828
14. 10-Helix with Click Chemistry J. Org. Chem. 2011, 76, 1228-1238
15. Yang, S.-H.; Lee, D.-J.; Brimble, M. A. Synthesis of an NDPK Phosphocarrier Domain Peptide Containing a Novel Triazolylalanine Analogue of Phosphohistidine Using Click Chemistry Org. Lett. 2011, 13, 5604-5607
16. Zhang, J.; Kemmink, J.; Rijkers, D. T. S.; Liskamp, R. M. Cu(I)- and Ru(II)-Mediated "Click" Cyclization of Tripeptides toward Vancomycin-Inspired Mimics Org. Lett. 2011, 13, 3438-3441
17. Pehere, A. D.; Abell, A. D. New β-Strand Templates Constrained by Huisgen Cycloaddition Org. Lett. 2012, 14, 1330-1333
18. Wu, C.-F.; Zhao, X.; Lan, W.-X.; Cao, C.; Liu, J.-T.; Jiang, X.-K.; Li, Z.-T. A 1,4-Diphenyl-1,2,3-Triazole-Based β-Turn Mimic Constructed by Click Chemistry J. Org. Chem. 2012, 77, 4261-4270
19. Buysse, K.; Farard, J.; Nikolaou, A.; Vanderheyden, P.; Vauquelin, G.; Pedersen, D. S.; Tourwe, D.; Ballet, S. Amino Triazolo Diazepines (Ata) as Constrained Histidine Mimics Org. Lett. 2011, 13, 6468-6471
20. Londregan, A. T.; Farley, K. A.; Limberakis, C.; Mullins, P. B.; Piotrowski, D. W. A New and Useful Method for the Macrocyclization of Linear Peptides Org. Lett. 2012, 14, 2890-2893
21. Culik, R. M.; Jo, H.; DeGrado, W. F.; Gai, F. Using Thioamides To Site-Specifically Interrogate the Dynamics of Hydrogen Bond Formation in β-Sheet Folding J. Am. Chem. Soc. 2012, 134, 8026-8029
22. Vishwanatha, T. M.; Narendra, N.; Chattopadhyay, B.; Mukherjee, M.; Sureshbabu, V. V. Synthesis of Selenoxo Peptides and Oligoselenoxo Peptides Employing LiAlHSeH J. Org. Chem. 2012, 77, 2689-2702
23. Yamagishi, T.; Tashiro, N.; Yokomatsu, T. Diastereoselective Synthesis of the Leu-Pro Type Phosphinyl Dipeptide Isostere J. Org. Chem. 2011, 76, 5472-5476
24. Turcotte, S.; Bouayad-Gervais, S. H.; Lubell, W. D. N -Aminosulfamide Peptide Mimic Synthesis by Alkylation of Aza-sulfurylglycinyl Peptides Org. Lett. 2012, 14, 1318-1321
25. Bo, Y.; Singh, S.; Duong, H. Q.; Cao, C.; Sieburth, S. McN. Efficient, Enantioselective Assembly of Silanediol Protease Inhibitors Org. Lett. 2011, 13, 1787-1789
26. Korendovych, I. V.; Shandler, S. J.; Montalvo, G. L.; DeGrado, W. F. Environment- and Sequence-Dependence of Helical Type in Membrane-Spanning Peptides Composed of β3-Amino Acids Org. Lett. 2011, 13, 3474-3477
27. Org. Lett. 2012, 14, 3236.
28. Andre, C.; Legrand, B.; Deng, C.; Didierjean, C.; Pickaert, G.; Martinez, J.; Averlant-Petit, M. C.; Amblard, M.; Calmes, M. (S)-ABOC: A Rigid Bicyclic β-Amino Acid as Turn Inducer Org. Lett. 2012, 14, 960-963
29. Lengyel, G. A.; Frank, R. C.; Horne, W. S. Hairpin Folding Behavior of Mixed α/β-Peptides in Aqueous Solution J. Am. Chem. Soc. 2011, 133, 4246-4249
30. Haase, H. S.; Peterson-Kaufman, K. J.; Lan-Levengood, S. K.; Checco, J. W.; Murphy, W. L.; Gellman, S. H. Extending Foldamer Design beyond α-Helix Mimicry: α/β-Peptide Inhibitors of Vascular Endothelial Growth Factor Signaling J. Am. Chem. Soc. 2012, 134, 7652-7655
31. Sanii, B.; Kudirka, R.; Cho, A.; Venkateswaran, N.; Olivier, G. K.; Olson, A. M.; Tran, H.; Harada, R. M.; Tan, L.; Zuckermann, R. N. Shaken, Not Stirred: Collapsing a Peptoid Monolayer To Produce Free-Floating, Stable Nanosheets J. Am. Chem. Soc. 2011, 133, 20808-20815
32. 3 Mineralization J. Am. Chem. Soc. 2011, 133, 5214-5217
33. Stringer, J. R.; Crapster, J. A.; Guzei, I. A.; Blackwell, H. E. Extraordinarily Robust Polyproline Type I Peptoid Helices Generated via the Incorporation of α-Chiral Aromatic N -1-Naphthylethyl Side Chains J. Am. Chem. Soc. 2011, 133, 15559-15567
34. Paul, B.; Butterfoss, G. L.; Boswell, M. G.; Huang, M. L.; Bonneau, R.; Wolf, C.; Kirshenbaum, K. N -Naphthyl Peptoid Foldamers Exhibiting Atropisomerism Org. Lett. 2012, 14, 926-929
35. Spiegel, J.; Mas-Moruno, C.; Kessler, H.; Lubell, W. D. Cyclic Aza-peptide Integrin Ligand Synthesis and Biological Activity J. Org. Chem. 2012, 77, 5271-5278
36. Sabatino, D.; Proulx, C.; Pohankova, P.; Ong, H.; Lubell, W. D Structure-Activity Relationships of GHRP-6 Azapeptide Ligands of the CD36 Scavenger Receptor by Solid-Phase Submonomer Azapeptide Synthesis J. Am. Chem. Soc. 2011, 133, 12493-12506
37. Freeman, N. S.; Tal-Gan, Y.; Klein, S.; Levitzki, A.; Gilon, C. Microwave-Assisted Solid-Phase Aza-Peptide Synthesis: Aza Scan of a PKB/Akt Inhibitor Using Aza-Arginine and Aza-Proline Precursors J. Org. Chem. 2011, 76, 3078-3085
38. Hanessian, S.; Chenard, E. A. New Approach to the Synthesis of Peptidomimetic Renin Inhibitors: Palladium-Catalyzed Asymmetric Allylation of Acyclic Alkyl Aryl Ketones Org. Lett. 2012, 14, 3222-3225
39. Raghuraman, A.; Ko, E.; Perez, L. M.; Ioerger, T. R.; Burgess, K. Pyrrolinone-Pyrrolidine Oligomers as Universal Peptidomimetics J. Am. Chem. Soc. 2011, 133, 12350-12353
40. Tadd, A. C.; Meinander, K.; Luthman, K.; Wallen, E. A. A. Synthesis of Orthogonally Protected Disulfide Bridge Mimetics J. Org. Chem. 2011, 76, 673-675
41. Krow, G. R.; Edupuganti, R.; Gandla, D.; Yu, F.; Sender, M.; Sonnet, P. E.; Zdilla, M. J.; DeBrosse, C.; Cannon, K. C.; Ross, C. W., III Synthesis of Conformationally Constrained 5-Fluoro- and 5-Hydroxymethanopyrrolidines. Ring-Puckered Mimics of Gauche-and Anti -3-Fluoro- and 3-Hydroxypyrrolidines J. Org. Chem. 2011, 76, 3626-3634
42. Sacchetti, A.; Silvani, A.; Lesma, G.; Pilati, T. Phe-Ala-Based Diazaspirocyclic Lactam As Nucleator of Type II′ β-Turn J. Org. Chem. 2011, 76, 833-839
43. Godina, T. A.; Lubell, W. D. Mimics of Peptide Turn Backbone and Side-Chain Geometry by a General Approach for Modifying Azabicyclo[5.3.0] alkanone Amino Acids J. Org. Chem. 2011, 76, 5846-5849
44. Lee, J. H.; Zhang, Q.; Jo, S.; Chai, S. C.; Oh, M.; Im, W.; Lu, H.; Lim, H.-S. Novel Pyrrolopyrimidine-Based α-Helix Mimetics: Cell-Permeable Inhibitors of Protein-Protein Interactions J. Am. Chem. Soc. 2011, 133, 676-679
45. Adler, M. J.; Hamilton, A. D. Oligophenylenaminones as Scaffolds for α-Helix Mimicry J. Org. Chem. 2011, 76, 7040-7047
46. Cheng, P.-N.; Nowick, J. S. Giant Macrolactams Based on β-Sheet Peptides J. Org. Chem. 2011, 76, 3166-3173
47. Liu, C.; Sawaya, M. R.; Cheng, P.-N.; Zheng, J.; Nowick, J. S.; Eisenberg, D. Characteristics of Amyloid-Related Oligomers Revealed by Crystal Structures of Macrocyclic β-Sheet Mimics J. Am. Chem. Soc. 2011, 133, 6736-6744
48. Wang, B.; Huang, P.-H.; Chen, C.-S.; Forsyth, C. J. Total Syntheses of the Histone Deacetylase Inhibitors Largazole and 2- epi -Largazole: Application of N -Heterocyclic Carbene Mediated Acylations in Complex Molecule Synthesis J. Org. Chem. 2011, 76, 1140-1150
49. Diness, F.; Nielsen, D. S.; Fairlie, D. P. Synthesis of the Thiazole-Thiazoline Fragment of Largazole Analogues J. Org. Chem. 2011, 76, 9845-9851
50. Okamoto, K.; Sakagami, M.; Feng, F.; Togame, H.; Takemoto, H.; Ichikawa, S.; Matsuda, A. Total Synthesis and Biological Evaluation of Pacidamycin D and Its 3′-Hydroxy Analogue J. Org. Chem. 2012, 77, 1367-1377
51. Sleebs, M. M.; Scanlon, D.; Karas, J.; Maharani, R.; Hughes, A. B. Total Synthesis of the Antifungal Depsipeptide Petriellin A J. Org. Chem. 2011, 76, 6686-6693
52. Hunter, L.; Chung, J. H. Total Synthesis of Unguisin A J. Org. Chem. 2011, 76, 5502-5505
53. Breazzano, S. P.; Boger, D. L. Synthesis and Stereochemical Determination of Complestatin A and B (Neuroprotectin A and B) J. Am. Chem. Soc. 2011, 133, 18495-18502
54. Aulakh, V. S.; Ciufolini, M. A. Total Synthesis and Complete Structural Assignment of Thiocillin I J. Am. Chem. Soc. 2011, 133, 5900-5904
55. Hall, E. A.; Kuru, E.; VanNieuwenhze, M. S. Solid-Phase Synthesis of Lysobactin (Katanosin B): Insights into Structure and Function Org. Lett. 2012, 14, 2730-2733
56. Garcia, J. M.; Curzon, S. S.; Watts, K. R.; Konopelski, J. P. Total Synthesis of Nominal (11 S)- and (11 R)-Cyclocinamide A Org. Lett. 2012, 14, 2054-2057
57. Singh, E. K.; Ramsey, D. M.; McAlpine, S. R. Total Synthesis of trans, trans -Sanguinamide B and Conformational Isomers Org. Lett. 2012, 14, 1198-1201
58. Benelkebir, H.; Donlevy, A. M.; Packham, G.; Ganesan, A. Total Synthesis and Stereochemical Assignment of Burkholdac B, a Depsipeptide HDAC Inhibitor Org. Lett. 2011, 13, 6334-6337
59. Ranatunga, S.; Kim, J. S.; Pal, U.; Del Valle, J. R. An Ester Enolate-Claisen Rearrangement Route to Substituted 4-Alkylideneprolines. Studies toward a Definitive Structural Revision of Lucentamycin A J. Org. Chem. 2011, 76, 8962-8976
60. Thompson, R. E.; Jolliffe, K. A.; Payne, R. J. Total Synthesis of Microcin B17 via a Fragment Condensation Approach Org. Lett. 2011, 13, 680-683
61. Carrillo, A. K.; VanNieuwenhze, M. S. Synthesis of the AviMeCys-Containing D-Ring of Mersacidin Org. Lett. 2012, 14, 1034-1037
62. Liu, W.; Chan, A. S. H.; Liu, H.; Cochrane, S. A.; Vederas, J. C. Solid Supported Chemical Syntheses of Both Components of the Lantibiotic Lacticin 3147 J. Am. Chem. Soc. 2011, 133, 14216-14219
63. Hsieh, Y. S. Y.; Wilkinson, B. L.; O'Connell, M. R.; MacKay, J. P.; Matthews, J. M.; Payne, R. J. Synthesis of the Bacteriocin Glycopeptide Sublancin 168 and S -Glycosylated Variants Org. Lett. 2012, 14, 1910-1913
64. Wang, F.; Qin, L.; Wong, P.; Gao, J. Facile Synthesis of Tetrafluorotyrosine and Its Application in pH Triggered Membrane Lysis Org. Lett. 2011, 13, 236-239
65. Knerr, P. J.; van der Donk, W. A. Chemical Synthesis and Biological Activity of Analogues of the Lantibiotic Epilancin 15X J. Am. Chem. Soc. 2012, 134, 7648-7651
66. Craik, D. J.; Conibear, A. C. The Chemistry of Cyclotides J. Org. Chem. 2011, 76, 4805-4817
67. Qiao, K.; Zhou, H.; Xu, W.; Zhang, W.; Garg, N.; Tang, Y. A Fungal Nonribosomal Peptide Synthetase Module that can Synthesize Thiopyrazines Org. Lett. 2011, 13, 1758-1761
68. Sahu, B.; Sacui, I.; Rapireddy, S.; Zanotti, K. J.; Bahal, R.; Armitage, B. A.; Ly, D. H. Synthesis and Characterization of Conformationally Preorganized, (R)-Diethylene Glycol-Containing γ-Peptide Nucleic Acids with Superior Hybridization Properties and Water Solubility J. Org. Chem. 2011, 76, 5614-5627
69. Nanda, M.; Ganesh, K. N. 4(R / S)-Guanidinylprolyl Collagen Peptides: On-Resin Synthesis, Complexation with Plasmid DNA, and the Role of Peptides in Enhancment of Transfection J. Org. Chem. 2012, 77, 4131-4135
70. Romney, D. K.; Miller, S. J. A Peptide-Embedded Trifluoromethyl Ketone Catalyst for Enantioselective Epoxidation Org. Lett. 2012, 14, 1138-1141
71. Haugaard-Kedstrom, L. M.; Shabanpoor, F.; Hossain, M. A.; Clark, R. J.; Ryan, P. J.; Craik, D. J.; Gundlach, A. L.; Wade, J. D.; Bathgate, R. A. D.; Rosengren, K. J. Design, Synthesis, and Characterization of a Single-Chain Peptide Antagonist for the Relaxin-3 Receptor RXFP3 J. Am. Chem. Soc. 2011, 133, 4965-4974