Open AccessSynthesis of Highly-strained Cyclic Tetrapeptides via Peptide Hydrazide Based Ligation
Author(s) -
Han Liu,
Xuechen Li
Publication year - 2014
Publication title -
huaxue xuebao
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.565
H-Index - 40
ISSN - 0567-7351
DOI - 10.6023/a14110820
Subject(s) - chemistry , hydrazide , cyclic peptide , ligation , peptide , chemical ligation , combinatorial chemistry , biophysics , biochemistry , organic chemistry , medicine , biology
A series of highly-strained cyclic tetrapeptides were efficiently synthesized via peptide hydrazide based ligation, reported by Liu et al. Upon mild oxidative activation, the peptide hydrazide was transformed into a highly active peptide azide intermediate and then in situ converted into a peptide 4-mercaptophenylacetic acid (MPAA) thiol ester, which underwent native chemical ligation (NCL)-mediated cyclization to afford the desired cyclic tetrapeptides. After radical desulfurization, the product with alanine residue at the ligation site can be obtained