Exploring Side-Chain Diversity by Submonomer Solid-Phase Aza-Peptide Synthesis
- 20 August 2009
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 11 (16) , 3650-3653
- https://doi.org/10.1021/ol901423c
Abstract
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 >= 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.This publication has 23 references indexed in Scilit:
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