Expedient synthesis of triazole-linked glycosyl amino acids and peptides.
[structure: see text] An expedient, high-yielding synthesis of two types of triazole-linked glycopeptides is described. These novel and stable glycopeptide mimics were prepared via Cu(I)-catalyzed [3 + 2] cycloaddition of either azide-functionalized glycosides and acetylenic amino acids or acetylenic glycosides and azide-containing amino acids.
Kuijpers
Brian H M
BH
Department of Organic Chemistry, NSRIM, University of Nijmegen, Toernooiveld 1, 6525 ED Nijmegen, The Netherlands.
Groothuys
Stan
S
Keereweer
A Bram R
AB
Quaedflieg
Peter J L M
PJ
Blaauw
Richard H
RH
van Delft
Floris L
FL
Rutjes
Floris P J T
FP
D000596:Amino Acids / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D006020:Glycopeptides / Q000032:analysis / Q000138:chemical synthesis* / Q000737:chemistry; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents; D015394:Molecular Structure; D014230:Triazoles / Q000138:chemical synthesis* / Q000737:chemistry
D000596:Amino Acids; D006020:Glycopeptides; D006027:Glycosides; D007202:Indicators and Reagents; D014230:Triazoles; D003300:Copper