Issue 37, 2017
From the journal:

Organic & Biomolecular Chemistry

Metal-free, direct conversion of α-amino acids into α-keto γ-amino esters for the synthesis of α,γ-peptides†

D. Hernández, ORCID logo *a   A. Boto, ORCID logo *a   D. Guzmána  and  E. Alvarez ORCID logo b  

* Corresponding authors

a Instituto de Productos Naturales y Agrobiología del CSIC, Avda. Astrofísico Francisco Sánchez 3, 38206-La Laguna, Tenerife, Spain
E-mail: alicia@ipna.csic.es

b Instituto de Investigaciones Químicas (CSIC-USe), Isla de la Cartuja, Avda. Américo Vespucio 49, 41092-Sevilla, Spain

Abstract

An efficient, metal-free synthesis of unusual α-keto γ-amino esters from α-amino acids is achieved by a radical scission–oxidation–addition of silyloxy acrylates procedure, where no purification of the reaction intermediates is needed. This protocol can be applied to the selective modification of the C-terminal position in peptides to give α,γ-hybrids.

Graphical abstract: Metal-free, direct conversion of α-amino acids into α-keto γ-amino esters for the synthesis of α,γ-peptides

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Article information

DOI
https://doi.org/10.1039/C7OB02033C
Article type
Communication
Submitted
15 Aug 2017
Accepted
22 Aug 2017
First published
23 Aug 2017

Org. Biomol. Chem., 2017,15, 7736-7742

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Metal-free, direct conversion of α-amino acids into α-keto γ-amino esters for the synthesis of α,γ-peptides

D. Hernández, A. Boto, D. Guzmán and E. Alvarez, Org. Biomol. Chem., 2017, 15, 7736 DOI: 10.1039/C7OB02033C

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