70396-27-9Relevant articles and documents
Coupling of sterically demanding peptides by β-thiolactone-mediated native chemical ligation
Chen, Huan,Xiao, Yunxian,Yuan, Ning,Weng, Jiaping,Gao, Pengcheng,Breindel, Leonard,Shekhtman, Alexander,Zhang, Qiang
, p. 1982 - 1988 (2018)
The ligation of sterically demanding peptidyl sites such as those involving Val-Val and Val-Pro linkages has proven to be extremely challenging with conventional NCL methods that rely on exogenous thiol additives. Herein, we report an efficient β-thiolactone-mediated additive-free NCL protocol that enables the establishment of these connections in good yield. The rapid NCL was followed by in situ desulfurization. Reaction rates between β-thiolactones and conventional thioesters towards NCL were also investigated, and direct aminolysis was ruled out as a possible pathway. Finally, the potent cytotoxic cyclic-peptide axinastatin 1 has been prepared using the developed methodology.
SEGMENT COUPLING IN PEPTIDE SYTHESIS-II A SIMPLE PREDICTIVE EQUATION CORRELATING RACEMIZATION AND PRIMARY STRUCTURE
Nguyen, Dung Le,Dormoy, Jean-Robert,Castro, Bertrand,Prevot, Daniel
, p. 4229 - 4238 (2007/10/02)
A predictive equation based on extrathermodynamic assumptions is proposed, that allows the prediction of the degree of epimerization in tripeptide model reactions of condensation of peptide segments as a function of the primary structure.The experimental