Synthesis of S-linked glycopeptides in aqueous solution.
Investigation of direct S-glycosylation of homocysteine and cysteine containing peptides with O-acetyl protected glycosyl halides led under two-phase conditions in the presence of sodium carbonate as base to excellent results. Thus, from glucosyl bromide, galactosyl bromide, lactosyl bromide, sialyl chloride, and N-Troc protected 2-amino-2-deoxyglucosyl bromide S-glycosylated dipeptides 15, 18-21, 23, 24, and 26-29, respectively, were obtained in excellent yields. Alternatively, depending on the solubility of the peptide moiety, mixtures of DMF and water could be employed for successfully carrying out this reaction. Thus, S-glycosylated tripeptides 42-45 could be obtained. Combination of this method with chemical ligation was also successfully carried out.
Zhu
Xiangming
X
Fachbereich Chemie, Universität Konstanz, Fach M 725, D-78457 Konstanz, Germany.
Pachamuthu
Kandasamy
K
Schmidt
Richard R
RR
D003545:Cysteine / Q000737:chemistry*; D006020:Glycopeptides / Q000138:chemical synthesis*; D006031:Glycosylation; D009842:Oligopeptides / Q000138:chemical synthesis; D012995:Solubility; D012996:Solutions
D006020:Glycopeptides; D009842:Oligopeptides; D012996:Solutions; D003545:Cysteine