Synthesis of stable triazole-linked glycopeptide mimics

ORGN 669

Floris P. J. T. Rutjes, f.rutjes@science.ru.nl1, Brian HM. Kuijpers, B.Kuijpers@science.ru.nl2, Stan Groothuys, s.groothuys@science.ru.nl2, Peter JLM. Quaedflieg3, Richard H. Blaauw, richard.blaauw@chiralix.com4, and Floris L. van Delft5. (1) Department of Organic Chemistry, Radboud University Nijmegen, Toernooiveld, Nijmegen, 6525 ED, Netherlands, (2) Institute for Molecules and Materials, Radboud University Nijmegen, Toernooiveld 1, Nijmegen, 6525 ED, Netherlands, (3) DSM Research, PO Box 18, Geleen, 6160 MD, Netherlands, (4) Chiralix B.V, Toernooiveld 100, 6525 EC Nijmegen, Netherlands, (5) Organic Chemistry, Radboud University Nijmegen, Toernooiveld 1, Nijmegen, 6525 ED, 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 azide-functionalized glycosides and acetylenic amino acids, or acetylenic glycosides and azide-containing amino acids. Beside the synthesis of the glyco amino acid derivatives, approaches will be highlighted for incorporation of these glyco amino acids into more complex glycopeptide structures.

 

New Reactions and Methodology
1:00 PM-5:00 PM, Wednesday, 16 March 2005 Convention Center -- Ballroom 20 C-D, Oral

Division of Organic Chemistry

The 229th ACS National Meeting, in San Diego, CA, March 13-17, 2005