Native N-glycopeptide Thioester Synthesis Through N→S Acyl Transfer
Overview
Affiliations
Peptide thioesters are important tools for the total synthesis of proteins using native chemical ligation (NCL). Preparation of glycopeptide thioesters, that enable the assembly of homogeneously glycosylated proteins, is complicated by the perceived fragile nature of the sugar moiety. Herein, we demonstrate the compatibility of thioester formation via N→S acyl transfer with native N-glycopeptides and report observations that will aid in their preparation.
Synthesis and anti-osteoporosis activity of novel Teriparatide glycosylation derivatives.
Wang N, Li J, Song H, Liu C, Hu H, Liao H RSC Adv. 2022; 10(43):25730-25735.
PMID: 35518599 PMC: 9055339. DOI: 10.1039/d0ra05136e.
Geiermann A, Micura R Chembiochem. 2012; 13(12):1742-5.
PMID: 22786696 PMC: 3430856. DOI: 10.1002/cbic.201200368.
Shifting Native Chemical Ligation into Reverse through N→S Acyl Transfer.
Macmillan D, Adams A, Premdjee B Isr J Chem. 2012; 51(8-9):885-899.
PMID: 22347724 PMC: 3277902. DOI: 10.1002/ijch.201100084.