期刊
JOURNAL OF PEPTIDE SCIENCE
卷 15, 期 11, 页码 731-737出版社
WILEY
DOI: 10.1002/psc.1164
关键词
4,5-dimethoxy-2-mercaptobenzyl (Dmmb) group; peptide thioester; N-S acyl shift; Fmoc SPPS; thioester-producing resin; on-resin preparation
资金
- Ministry of Education, Culture, Sports, Science and Technology, Japan [15083204, 17750158, 18310145]
- Grants-in-Aid for Scientific Research [18310145, 15083204, 17750158] Funding Source: KAKEN
An efficient method of peptide thioester synthesis is described. The reaction is based on an N-4,5-dimethoxy-2-mercaptobenzyl (Dmmb) auxiliary-assisted N-S acyl shift reaction after assembling a peptide chain by Fmoc-solid phase peptide synthesis. The Dmmb-assisted N-S acyl shift reaction proceeded efficiently under mildly acidic conditions, and the peptide thioester was obtained by treating the resulting S-peptide with sodium 2-mercaptoethanesulfonate. No detectable epimerization of the amino acid residue adjacent to the thioester moiety in the case of Leu was found. The reactions were also amenable to the on-resin preparation of peptide thioesters. The utility was demonstrated by the synthesis of a 41-mer peptide thioester, a phosphorylated peptide thioester and a 33-mer peptide thioester containing a trimethylated lysine residue. Copyright (C) 2009 European Peptide Society and John Wiley & Sons, Ltd.
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