Efficient synthesis of triazole-containing glycopeptide mimics

ORGN 940

Stan Groothuys, s.groothuys@science.ru.nl1, Brian HM. Kuijpers, B.Kuijpers@science.ru.nl1, Peter JLM. Quaedflieg2, Richard H. Blaauw, richard.blaauw@chiralix.com3, Floris L. van Delft1, and Floris P. J. T. Rutjes1. (1) Institute for Molecules and Materials, Radboud University Nijmegen, Toernooiveld 1, Nijmegen, 6525 ED, Netherlands, (2) DSM Research, PO Box 18, Geleen, 6160 MD, Netherlands, (3) Chiralix B.V, Toernooiveld 100, 6525 EC Nijmegen, Netherlands
Efficient syntheses of different types of triazole-linked glycopeptides will be described. These novel and stable glycopeptide mimics were prepared via Cu(I)-catalyzed [3+2] cycloaddition of either acetylenic glycosides and azide-containing amino acids or peptides, or azide-functionalized glycosides and acetylenic amino acids or peptides. Besides, approaches will be highlighted for the enzymatic synthesis of larger glycopeptide structures and attention will be paid to their biological activity.

 

Proteins, Peptides, Amino Acids, and Enzyme Inhibitors
1:00 PM-5:00 PM, Thursday, 14 September 2006 Moscone Center -- Room 131, Oral

Division of Organic Chemistry

The 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006