Issue 14, 2010
From the journal:

Organic & Biomolecular Chemistry

A new tool for photoaffinity labeling studies: a partially constrained, benzophenone based, α-amino acid†

Karen Wright,*a   Alessandro Moretto,b   Marco Crisma,b   Michel Wakselman,a   Jean-Paul Mazaleyrat,a   Fernando Formaggiob  and  Claudio Toniolo*b  

* Corresponding authors

a ILV, UMR CNRS 8180, University of Versailles, 78035 Versailles, France
E-mail: wright@chimie.uvsq.fr
Fax: +33 01 3925 4452
Tel: +33 01 3925 4366

b ICB, Padova Unit, CNR, Department of Chemistry, University of Padova, 35131 Padova, Italy
E-mail: claudio.toniolo@unipd.it
Fax: +39 049 827 5239
Tel: +39 049 827 5247

Abstract

The novel α-amino acid BpAib, a partially conformationally restricted analogue of the currently extensively used 3-(4-benzoylphenyl)alanine (Bpa) photoaffinity label, was synthesized, optically resolved, fully characterized, and appropriately derivatized. An intermolecular photocrosslinking experiment highlighted its regioselective reactivity towards the S-methyl side-chain group of a Met-based dipeptide, which is closely comparable to that of Bpa.

Graphical abstract: A new tool for photoaffinity labeling studies: a partially constrained, benzophenone based, α-amino acid

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Article information

DOI
https://doi.org/10.1039/C003943H
Article type
Paper
Submitted
09 Mar 2010
Accepted
13 May 2010
First published
26 May 2010

Org. Biomol. Chem., 2010,8, 3281-3286

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A new tool for photoaffinity labeling studies: a partially constrained, benzophenone based, α-amino acid

K. Wright, A. Moretto, M. Crisma, M. Wakselman, J. Mazaleyrat, F. Formaggio and C. Toniolo, Org. Biomol. Chem., 2010, 8, 3281 DOI: 10.1039/C003943H

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