Native N-glycopeptide thioester synthesis through N→S acyl transfer

Bioorganic and Medicinal Chemistry Letters

Volumn 21, Issue 17, 2011, Pages 4973-4975

  Premdjee, Bhavesh ^a   Adams, Anna L ^a   MacMillan, Derek ^a  

^a UNIVERSITY COLLEGE LONDON   (United Kingdom)

Author keywords

Glycopeptides; Native chemical ligation; Peptide thioesters

Indexed keywords

CYSTEINE; N GLYCOPEPTIDE THIOESTER; THIOESTER; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; CARBOXY TERMINAL SEQUENCE; EPIMERIZATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NATIVE CHEMICAL LIGATION; PEPTIDE SYNTHESIS; PROTEIN ANALYSIS; PROTEIN MODIFICATION; PROTEIN STRUCTURE;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; ESTERS; GLYCOPEPTIDES; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

EID: 80051799020     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2011.05.059     Document Type: Article

References (30)

1. H. Hojo, and Y. Nakahara Peptide Sci. 88 2007 308
2. T.J. Boltje, T. Buskas, and G.-J. Boons Nat. Chem. 1 2009 611
3. D.P. Gamblin, E.M. Scanlan, and B.G. Davis Chem. Rev. 109 2009 131
4. P.H. Seeberger Nat. Chem. Biol. 5 2009 368
5. P. Wang, and S.J. Danishefsky J. Am. Chem. Soc. 132 2010 17045
6. C. Kan, and S.J. Danishefsky Tetrahedron 65 2009 9047
7. K. Hirano, D. Macmillan, K. Tezuka, T. Tsuji, and Y. Kajihara Angew. Chem., Int. Ed. 48 2009 9557
8. N. Yamamoto, Y. Tanabe, R. Okamoto, P.E. Dawson, and Y. Kajihara J. Am. Chem. Soc. 130 2008 501
9. C. Piontek, D.V. Silva, C. Heinlein, C. Pöhner, S. Mezzato, P. Ring, A. Martin, Franz X. Schmid, and C. Unverzagt Angew. Chem., Int. Ed. 48 2009 1941
10. C. Piontek, P. Ring, O. Harjes, C. Heinlein, S. Mezzato, N. Lombana, C. Pöhner, M. Püttner, D.V. Silva, A. Martin, Franz X. Schmid, and C. Unverzagt Angew. Chem., Int. Ed. 48 2009 1936
11. D. Macmillan, and C.R. Bertozzi Angew. Chem., Int. Ed. 43 2004 1355
12. Y. Shin, K.A. Winans, B.J. Backes, S.B.H. Kent, J.A. Ellman, and C.R. Bertozzi J. Am. Chem. Soc. 121 1999 11684
13. S. Mezzato, M. Schaffrath, and C. Unverzagt Angew. Chem., Int. Ed. 44 2005 1650
14. C. Ozawa, H. Katayama, H. Hojo, Y. Nakahara, and Y. Nakahara Org. Lett. 10 2008 3531
15. K. Hirano, and Y. Kajihara J. Carbohydr. Chem. 29 2010 84
16. J. Kang, J.P. Richardson, and D. Macmillan Chem. Commun. 2009 407
17. J. Kang, N.L. Reynolds, C. Tyrrell, J.R. Dorin, and D. Macmillan Org. Biomol. Chem. 7 2009 4918
18. D. Macmillan, and L. Arham J. Am. Chem. Soc. 126 2004 9530
19. F. Burlina, D.D. Dixson, R.P. Doyle, G. Chassaing, C.N. Boddy, P. Dawson, and J. Offer Chem. Commun. 2008 2785
20. F. Schwarz, W. Huang, C. Li, B.L. Schulz, C. Lizak, A. Palumbo, S. Numao, D. Neri, M. Aebi, and L.-X. Wang Nat. Chem. Biol. 6 2010 264
21. L.-X. Wang, and W. Huang Curr. Opin. Chem. Biol. 13 2009 592
22. J. Kang, and D. Macmillan Org. Biomol. Chem. 8 2010 1993
23. T. Kawakami, S. Shimizu, and S. Aimoto Bull. Chem. Soc. Jpn. 83 2010 570
24. K.i. Nakamura, M. Sumida, T. Kawakami, T. Vorherr, and S. Aimoto Bull. Chem. Soc. Jpn. 79 2006 1773
25. H. Hojo, Y. Onuma, Y. Akimoto, Y. Nakahara, and Y. Nakahara Tetrahedron Lett. 48 2007 25
26. S. Tsuda, A. Shigenaga, K. Bando, and A. Otaka Org. Lett. 11 2009 823
27. Y. Ohta, S. Itoh, A. Shigenaga, S. Shintaku, N. Fujii, and A. Otaka Org. Lett. 8 2006 467
28. L. Saleh, and F.B. Perler Chem. Rec. 6 2006 183
29. J.-P. Pellois, and T.W. Muir Curr. Opin. Chem. Biol. 10 2006 487
30. H.D. Mootz Chembiochem 10 2009 2579