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Solid-phase Submonomer Synthesis of Peptoid Polymers and their Self-Assembly into Highly-Ordered Nanosheets
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Published on: November 2, 2011

Exploring side-chain diversity by submonomer solid-phase aza-peptide synthesis.

David Sabatino1, Caroline Proulx, Sophie Klocek

  • 1Université de Montréal, Department of Chemistry, C.P. 6128 Succursale Centre-Ville, Montreal, Quebec, Canada H3C 3J7.

Organic Letters
|July 18, 2009
PubMed
Summary

Researchers developed a novel method for synthesizing aza-peptides, creating analogues of Growth Hormone Releasing Peptide-6 (GHRP-6). One analogue showed significantly improved selectivity for the CD36 receptor, highlighting potential for new therapeutic strategies.

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Solid Phase Synthesis of a Functionalized Bis-Peptide Using "Safety Catch" Methodology

Published on: May 15, 2012

Area of Science:

  • Medicinal Chemistry
  • Peptide Synthesis
  • Biotechnology

Background:

  • Growth Hormone Releasing Peptide-6 (GHRP-6) is a peptide with significant biological activity.
  • Developing selective analogues of biologically active peptides is crucial for targeted therapies.
  • Existing methods for aza-peptide synthesis can be complex and involve hazardous reagents.

Purpose of the Study:

  • To develop a versatile and efficient method for synthesizing aza-peptide analogues.
  • To create novel aza-analogues of GHRP-6.
  • To investigate the structure-activity relationships of these novel aza-peptides.

Main Methods:

  • Submonomer synthesis approach utilizing regioselective alkylation of peptide-bound aza-Gly residues.
  • Synthesis of ten aza-analogues of GHRP-6.
  • Circular dichroism spectroscopy to determine secondary structure.

Main Results:

  • Ten aza-analogues of GHRP-6 were synthesized with yields ranging from 15-42% and purity generally >=90%.
  • AzaPhe-peptide 7a was found to induce a beta-turn conformation.
  • AzaPhe-peptide 7a exhibited a 1000-fold improvement in GHRP-6 selectivity for the CD36 receptor.

Conclusions:

  • The developed submonomer synthesis is a versatile method for creating aza-peptides, avoiding solution-phase hydrazine synthesis.
  • The findings suggest that conformational changes, such as beta-turns, can significantly enhance receptor selectivity.
  • This method is well-suited for studying side-chain-activity relationships in biologically active peptides, paving the way for optimized therapeutics.