Access to α,α-Disubstituted Disilylated Amino Acids and Their Use in Solid-Phase Peptide Synthesis

Organic Letters
Roberto FanelliFlorine Cavelier

Abstract

A concise synthetic pathway yielding to hydrophobic α,α-disubstituted disilylated amino acids based on a hydrosilylation reaction is described. As a first example of utilization in solid-phase peptide synthesis, TESDpg was introduced in replacement of Aib in an alamethicin sequence, leading to analogues with modified physicochemical properties and conserved helical structures. This study highlights the potential of these new amino acids as tools for peptide modulation.

References

Dec 19, 2000·Acta Crystallographica. Section C, Crystal Structure Communications·B VivetA Aubry
Mar 21, 2002·Journal of the American Chemical Society·Florine CavelierMichel Marraud
Nov 5, 2002·Biophysical Journal·D Peter TielemanMark S P Sansom
Mar 31, 2004·The Journal of Peptide Research : Official Journal of the American Peptide Society·F CavelierS Sagan
Mar 22, 2005·Protein and Peptide Letters·Jean Michel Brunel
Jun 29, 2006·Journal of the American Chemical Society·Sílvia PujalsErnest Giralt
Jan 26, 2007·Organic & Biomolecular Chemistry·Henning Vogt, Stefan Bräse
Jun 26, 2007·Chemistry & Biodiversity·Cristina PeggionClaudio Toniolo
May 8, 2009·Chemical Society Reviews·Matthew MortensenCarsten Bolm
Oct 18, 2011·Amino Acids·C MartinF Cavelier
Oct 16, 2012·Journal of Medicinal Chemistry·Annaliese K Franz, Sean O Wilson
Apr 9, 2013·The Journal of Physical Chemistry. C, Nanomaterials and Interfaces·Pei YangZhan Chen
Jul 31, 2013·Biopolymers·Cristina PeggionClaudio Toniolo
Mar 14, 2014·Organic Letters·Khoubaib Ben Haj Salah, Nicolas Inguimbert
Sep 13, 2014·Chemistry : a European Journal·Charlotte MartinFlorine Cavelier
Dec 3, 2014·Bioorganic & Medicinal Chemistry Letters·Andrea StevenazziMaria Lattanzio
Feb 27, 2015·Amino Acids·Roberto FanelliFlorine Cavelier

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Citations

Apr 26, 2018·Organic & Biomolecular Chemistry·Khoubaib Ben Haj SalahNicolas Inguimbert

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