Issue 4, 2013

Synthesis of cyclically constrained sugar derived α/β- and α/γ-peptides

Abstract

A general approach to enantiopure conformationally constrained sugar derived α/β- and α/γ-peptides has been established. Five-membered ring α/β-peptides were synthesized via formyl C-glycofuranosides, easy available from hexose-derived azido-2-equatorial-OH-glycopyranosides by DAST-promoted ring contraction. By means of a regioselective oxidation with TEMPO at C-6 of hexose-derived 3-azido glycopyranosides as the key step, two- and three-residue α/γ-peptides having a six-membered ring were obtained in good yields and under very simple experimental conditions.

Graphical abstract: Synthesis of cyclically constrained sugar derived α/β- and α/γ-peptides

Supplementary files

Article information

Article type
Paper
Submitted
12 Oct 2012
Accepted
13 Nov 2012
First published
13 Nov 2012

Org. Biomol. Chem., 2013,11, 676-686

Synthesis of cyclically constrained sugar derived α/β- and α/γ-peptides

A. Franconetti, S. Jatunov, P. Borrachero, M. Gómez-Guillén and F. Cabrera-Escribano, Org. Biomol. Chem., 2013, 11, 676 DOI: 10.1039/C2OB26992A

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements