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

Roberto Fanelli; Khoubaib Ben Haj Salah; Nicolas Inguimbert; Claude Didierjean; Jean Martinez; Florine Cavelier

doi:10.1021/acs.orglett.5b02175

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

Roberto Fanelli ¹ Khoubaib Ben Haj Salah ² Nicolas Inguimbert ² Claude Didierjean ³ Jean Martinez ¹ Florine Cavelier ¹

1 IBMM - Institut des Biomolécules Max Mousseron [Pôle Chimie Balard]

2 CRIOBE - Centre de recherches insulaires et observatoire de l'environnement

3 CRM2 - Cristallographie, Résonance Magnétique et Modélisations

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.

Type de document :

Article dans une revue

Organic Letters, American Chemical Society, 2015, 17 (18), 〈10.1021/acs.orglett.5b02175〉

Domaine :

Chimie / Chimie organique

Liste complète des métadonnées

https://hal-univ-perp.archives-ouvertes.fr/hal-01212249
Contributeur : Olivier Savoyat <>
Soumis le : mardi 6 octobre 2015 - 13:14:22
Dernière modification le : jeudi 11 janvier 2018 - 06:23:18

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

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