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Photorelease of tyrosine from a-carboxy-6-nitroveratryl (aCNV) derivatives

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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.

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Authors and Affiliations

  1. School of Chemistry, University of Birmingham, Edgbaston, Birmingham, UK, B15 2TT

    Alexander G. Russell, Matthew J. Sadler, Helen J. Laidlaw, Agustín Gutiérrez-Loriente & John S. Snaith

  2. School of Biosciences, University of Birmingham, Edgbaston, Birmingham, UK, B15 2TT

    Christopher W. Wharton

  3. ISM CNRS UMR 5255, Université Bordeaux 1, 33405, Talence, France

    David Carteau & Dario M. Bassani

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  1. Alexander G. Russell
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  2. Matthew J. Sadler
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Correspondence to Dario M. Bassani or John S. Snaith.

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Russell, A.G., Sadler, M.J., Laidlaw, H.J. et al. Photorelease of tyrosine from a-carboxy-6-nitroveratryl (aCNV) derivatives. Photochem Photobiol Sci 11, 556–563 (2012). https://doi.org/10.1039/c2pp05320a

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  • DOI: https://doi.org/10.1039/c2pp05320a

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