70396-27-9Relevant academic research and scientific papers
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.
Intramolecular ligation of carbonyl oxygen to central zinc in synthetic oligopeptide-linked zinc-porphyrins
Tamiaki,Kiyomori,Maruyama
, p. 2478 - 2486 (2007/10/02)
Oligopeptide-linked zinc-porphyrins were prepared (oligopeptide = -Phe(m)-Ala(n)-OMe and porphyrin = 5,15-diaryl-2,3,7,8,12,13,17,18-octaethylporphyrin). 1H NMR, IR, visible, and CD spectra of the synthetic molecule in a chlorinated methane (CDCl3 or CH2Cl2) showed that the carbonyl oxygen of the N-terminal amino acid of the linked peptide should ligate the central zine metal in the molecule as the axial ligand to form a pentacoordinated zinc-porphyrin. The coordination of the zinc with the peptide framework changed the optical and electrical properties, indicating that such ligation might control the reactivity in biological metallotetrapyrrole-protein systems as well as the coordination to the peptide residue.
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
