Academic Scholarship

Exploring Side-Chain Diversity by Submonomer Aza-peptide Synthesis

Organic Letters, 11(16), 3650- 3653, July 2009

Photo Needed David Sabatino, Ph.D.
Department of Chemistry and Biochemistry
Caroline Proulx, Sophie Klocek, Carine B. Bourguet, Damien Boeglin, Huy Ong and William D. Lubell

Submonomer synthesis of aza-peptides featuring regioselective alkylation of peptide-bound aza-Gly residues provided ten aza-analogues of the Growth Hormone Releasing Peptide-6 (GHRP-6) in 15-42% yield and purity generally >or=90%. Circular dichroism demonstrated that azaPhe-peptide 7a induced a beta-turn conformation which may be responsible for its 1000-fold improvement in GHRP-6 selectivity for the CD36 receptor. This versatile method for making aza-peptides avoids solution-phase hydrazine synthesis and is well suited for studying side-chain-activity relationships of biologically active peptides.


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