Convergent synthesis of peptide conjugates using dehydroalanines for chemoselective ligations.
[reaction: see text]. Protein and peptide conjugates such as glycopeptides, prenylated peptides, and lipopeptides play essential roles in biology. A rapid and convergent entry into a variety of these compounds is described. The methodology involves the introduction of a dehydroalanine into peptides and subsequent chemoselective conjugate addition of an appropriate thiolate nucleophile, including farnesylthiolate or thioglycosides.
Zhu
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Y
Department of Chemistry, University of Illinois at Urbana-Champaign, 600 South Mathews Avenue, Urbana, Illinois 61801, USA.
van der Donk
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WA
D000409:Alanine / Q000031:analogs & derivatives* / Q000737:chemistry*; D008026:Ligation; D008956:Models, Chemical; D010452:Peptide Biosynthesis; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D017368:Protein Prenylation; D013438:Sulfhydryl Compounds / Q000737:chemistry; D013865:Thioglycosides / Q000737:chemistry
D010455:Peptides; D013438:Sulfhydryl Compounds; D013865:Thioglycosides; C015102:dehydroalanine; D000409:Alanine