Issue 3, 2012
From the journal:

Photochemical & Photobiological Sciences

Photorelease of tyrosine from α-carboxy-6-nitroveratryl (αCNV) derivatives†‡

Alexander G. Russell,a   Matthew J. Sadler,a   Helen J. Laidlaw,a   Agustín Gutiérrez-Loriente,a   Christopher W. Wharton,b   David Carteau,c   Dario M. Bassani*c  and  John S. Snaith*a  

* Corresponding authors

a School of Chemistry, University of Birmingham, Edgbaston, Birmingham, U.K.
E-mail: j.s.snaith@bham.ac.uk

b School of Biosciences, University of Birmingham, Edgbaston, Birmingham, U.K.

c ISM CNRS UMR 5255, Université Bordeaux 1, Talence, France
E-mail: d.bassani@ism.u-bordeaux1.fr

Abstract

The synthesis of photolabile tyrosine derivatives protected on the phenolic oxygen by the α-carboxy-6-nitroveratryl (αCNV) protecting group is described. The compounds undergo rapid photolysis at wavelengths longer than 300 nm to liberate the corresponding phenol in excellent yield (quantum yield for the deprotection of tyrosine = 0.19). Further protection of caged tyrosine is possible, yielding N-Fmoc protected derivatives suitable for direct incorporation of caged tyrosine in solid-phase peptide synthesis.

Graphical abstract: Photorelease of tyrosine from α-carboxy-6-nitroveratryl (αCNV) derivatives

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Article information

DOI
https://doi.org/10.1039/C2PP05320A
Article type
Paper
Submitted
29 Sep 2011
Accepted
30 Nov 2011
First published
17 Jan 2012

Photochem. Photobiol. Sci., 2012,11, 556-563

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Photorelease of tyrosine from α-carboxy-6-nitroveratryl (αCNV) derivatives

A. G. Russell, M. J. Sadler, H. J. Laidlaw, A. Gutiérrez-Loriente, C. W. Wharton, D. Carteau, D. M. Bassani and J. S. Snaith, Photochem. Photobiol. Sci., 2012, 11, 556 DOI: 10.1039/C2PP05320A

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