Rapid Synthesis of Acyl Transfer Auxiliaries for Cysteine-Free Native Glycopeptide Ligation
- 17 November 2004
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 6 (25) , 4659-4662
- https://doi.org/10.1021/ol048145o
Abstract
[reaction: see text] Rapid, facile routes to the TFA-cleavable 4,5,6-trimethoxy-2-mercaptobenzyl and 1-(2,4-dimethoxyphenyl)-2-mercaptoethyl classes of auxiliaries for cysteine-free native chemical ligation are described. Rapid synthesis, coupled with mild cleavage conditions will undoubtedly broaden the utility of such auxiliaries, particularly where chemically fragile peptide modifications such as glycosylation are present.Keywords
This publication has 22 references indexed in Scilit:
- An o-nitrobenzyl scaffold for peptide ligation: synthesis and applicationsBioorganic & Medicinal Chemistry, 2004
- Derivatized Amino Acids Relevant to Native Peptide Synthesis by Chemical Ligation and Acyl TransferThe Journal of Organic Chemistry, 2003
- Extending Synthetic Access to Proteins with a Removable Acyl Transfer AuxiliaryJournal of the American Chemical Society, 2002
- Total synthesis of cytochrome b562 by native chemical ligation using a removable auxiliaryProceedings of the National Academy of Sciences, 2001
- Native chemical ligation using removable Nα-(1-phenyl-2-mercaptoethyl) auxiliariesTetrahedron Letters, 2001
- Synthesis of Native Proteins by Chemical LigationAnnual Review of Biochemistry, 2000
- Nα-2-Mercaptobenzylamine-Assisted Chemical LigationOrganic Letters, 1999
- Extending the Applicability of Native Chemical LigationJournal of the American Chemical Society, 1996
- Synthesis of Proteins by Native Chemical LigationScience, 1994
- Peptide segment ligation strategy without use of protecting groups.Proceedings of the National Academy of Sciences, 1994