Rapid synthesis of acyl transfer auxiliaries for cysteine-free native glycopeptide ligation.
[reaction: see text] Rapid, facile routes to the TFA-cleavable 4,5,6-trimethoxy-2-mercaptobenzyl and 1-(2,4-dimethoxyphenyl)-2-mercaptoethyl classes of auxiliaries for cysteine-free native chemical ligation are described. Rapid synthesis, coupled with mild cleavage conditions will undoubtedly broaden the utility of such auxiliaries, particularly where chemically fragile peptide modifications such as glycosylation are present.
Macmillan
Derek
D
School of Chemistry, University of Edinburgh, Kings Buildings, West Mains Road, Edinburgh, EH9 3JJ, Scotland, UK. derek.macmillan@ed.ac.uk
Anderson
David W
DW
D002384:Catalysis; D002851:Chromatography, High Pressure Liquid; D003545:Cysteine / Q000737:chemistry*; D006020:Glycopeptides / Q000138:chemical synthesis*; D010165:Palladium / Q000737:chemistry; D013438:Sulfhydryl Compounds / Q000737:chemistry
D006020:Glycopeptides; D013438:Sulfhydryl Compounds; D010165:Palladium; D003545:Cysteine