Rapid Additive-Free Selenocystine-Selenoester Peptide Ligation

Journal of the American Chemical Society

Volumn 137, Issue 44, 2015, Pages 14011-14014

  Mitchell, Nicholas J ^a   Malins, Lara R ^a   Liu, Xuyu ^a   Thompson, Robert E ^a   Chan, Bun ^a   Radom, Leo ^a   Payne, Richard J ^a  

^a UNIVERSITY OF SYDNEY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITIVES; BIOSYNTHESIS; DIMERS; PEPTIDES; SURGICAL EQUIPMENT; SYNTHESIS (CHEMICAL);

AMIDE BOND; AQUEOUS BUFFER; COMPUTATIONAL STUDIES; N-TERMINALS; ONE POT; PEPTIDE LIGATIONS; SELENOCYSTINE; TOTAL SYNTHESIS;

SELENIUM COMPOUNDS;

AMIDE; PEPTIDE; SELENOCYSTINE; SELENOESTER PEPTIDE; UNCLASSIFIED DRUG; BACTERIAL ANTIGEN; BACTERIAL PROTEIN; CHORISMATE MUTASE; CYSTINE; ESAT-6 PROTEIN, MYCOBACTERIUM TUBERCULOSIS; ESTER; ORGANOSELENIUM DERIVATIVE; SELENIUM DERIVATIVE;

AMINO TERMINAL SEQUENCE; ARTICLE; CHEMICAL REACTION; DESELENIZATION; ONE POT SYNTHESIS; PH; ANALOGS AND DERIVATIVES; CHEMISTRY; CONFORMATION; ENZYMOLOGY; METABOLISM; MYCOBACTERIUM TUBERCULOSIS; SYNTHESIS;

ANTIGENS, BACTERIAL; BACTERIAL PROTEINS; CHORISMATE MUTASE; CYSTINE; ESTERS; MOLECULAR CONFORMATION; MYCOBACTERIUM TUBERCULOSIS; ORGANOSELENIUM COMPOUNDS; PEPTIDES; SELENIUM COMPOUNDS;

EID: 84947461299     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.5b07237     Document Type: Article

References (35)

1. Dawson, P. E.; Muir, T. W.; Clark-Lewis, I.; Kent, S. B. H. Science 1994, 266, 776 10.1126/science.7973629
2. Kent, S. B. H. Chem. Soc. Rev. 2009, 38, 338 10.1039/B700141J
3. Dawson, P. E.; Churchill, M. J.; Ghadiri, M. R.; Kent, S. B. H. J. Am. Chem. Soc. 1997, 119, 4325 10.1021/ja962656r
4. Johnson, E. C. B.; Kent, S. B. H. J. Am. Chem. Soc. 2006, 128, 6640 10.1021/ja058344i
5. Malins, L. R.; Payne, R. J. Aust. J. Chem. 2015, 68, 521 10.1071/CH14568
6. Yan, L. Z.; Dawson, P. E. J. Am. Chem. Soc. 2001, 123, 526 10.1021/ja003265m
7. Wan, Q.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2007, 46, 9248 10.1002/anie.200704195
8. Rohde, H.; Seitz, O. Biopolymers 2010, 94, 551 10.1002/bip.21442
9. Hackenberger, C. P. R.; Schwarzer, D. Angew. Chem., Int. Ed. 2008, 47, 10030 10.1002/anie.200801313
10. Dawson, P. E. Isr. J. Chem. 2011, 51, 862 10.1002/ijch.201100128
11. Malins, L. R.; Payne, R. J. Curr. Opin. Chem. Biol. 2014, 22, 70 10.1016/j.cbpa.2014.09.021
12. Hackeng, T. M.; Griffin, J. H.; Dawson, P. E. Proc. Natl. Acad. Sci. U. S. A. 1999, 96, 10068 10.1073/pnas.96.18.10068
13. For selective desulfurization of β-thiol Asp see: Thompson, R. E.; Chan, B.; Radom, L.; Jolliffe, K. A.; Payne, R. J. Angew. Chem., Int. Ed. 2013, 52, 9723 10.1002/anie.201304793
14. Hondal, R. J.; Nilsson, B. L.; Raines, R. T. J. Am. Chem. Soc. 2001, 123, 5140 10.1021/ja005885t
15. Gieselman, M. D.; Xie, L.; van der Donk, W. A. Org. Lett. 2001, 3, 1331 10.1021/ol015712o
16. Quaderer, R.; Sewing, A.; Hilvert, D. Helv. Chim. Acta 2001, 84, 1197 10.1002/1522-2675(20010516)84:5<1197::AID-HLCA1197>3.0.CO;2-#
17. Malins, L. R.; Mitchell, N. J.; McGowan, S.; Payne, R. J. Angew. Chem., Int. Ed. 2015, 54, 12716 10.1002/anie.201504639
18. Townsend, S. D.; Tan, Z.; Dong, S.; Shang, S.; Brailsford, J. A.; Danishefsky, S. J. J. Am. Chem. Soc. 2012, 134, 3912 10.1021/ja212182q
19. Malins, L. R.; Payne, R. J. Org. Lett. 2012, 14, 3142 10.1021/ol3012265
20. Malins, L. R.; Mitchell, N. J.; Payne, R. J. J. Pept. Sci. 2014, 20, 64 10.1002/psc.2581
21. Besse, D.; Siedler, F.; Diercks, T.; Kessler, H.; Moroder, L. Angew. Chem., Int. Ed. Engl. 1997, 36, 883 10.1002/anie.199708831
22. Metanis, N.; Keinan, E.; Dawson, P. E. Angew. Chem., Int. Ed. 2010, 49, 7049 10.1002/anie.201001900
23. Durek, T.; Alewood, P. F. Angew. Chem., Int. Ed. 2011, 50, 12042 10.1002/anie.201105512
24. Pollock, S. B.; Kent, S. B. H. Chem. Commun. 2011, 47, 2342 10.1039/C0CC04120C
25. McGrath, N. A.; Raines, R. T. Acc. Chem. Res. 2011, 44, 752 10.1021/ar200081s
26. Lukesh, J. C., 3rd; VanVeller, B.; Raines, R. T. Angew. Chem., Int. Ed. 2013, 52, 12901 10.1002/anie.201307481
27. Adams, A. L.; Macmillan, D. J. Pept. Sci. 2013, 19, 65 10.1002/psc.2469
28. Ollivier, N.; Blanpain, A.; Boll, E.; Raibaut, L.; Drobecq, H.; Melnyk, O. Org. Lett. 2014, 16, 4032 10.1021/ol501866j
29. Pfenninger, J.; Heuberger, C.; Graf, W. Helv. Chim. Acta 1980, 63, 2328 10.1002/hlca.19800630823
30. Boger, D. L.; Mathvink, R. J. J. Org. Chem. 1988, 53, 3377 10.1021/jo00249a053
31. Crich, D.; Fortt, S. M. Tetrahedron Lett. 1988, 29, 2585 10.1016/S0040-4039(00)86118-3
32. Ji, S.; Cao, W.; Yu, Y.; Xu, H. Angew. Chem., Int. Ed. 2014, 53, 6781 10.1002/anie.201403442
33. Prakash, P.; Aruna, B.; Sardesai, A. A.; Hasnain, S. E. J. Biol. Chem. 2005, 280, 19641 10.1074/jbc.M413026200
34. Sorensen, A. L.; Nagai, S.; Houen, G.; Andersen, P.; Andersen, A. B. Infect. Immun. 1995, 63, 1710
35. Thompson, R. E.; Liu, X.; Alonso-García, N.; Pereira, P. J. B.; Jolliffe, K. A.; Payne, R. J. J. Am. Chem. Soc. 2014, 136, 8161 10.1021/ja502806r