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

AG Russell; MJ Sadler; HJ Laidlaw; A Gutiérrez-Loriente; Christopher Wharton; D Carteau; DM Bassani; John Snaith

doi:10.1039/c2pp05320a

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

AG Russell, MJ Sadler, HJ Laidlaw, A Gutiérrez-Loriente, Christopher Wharton, D Carteau, DM Bassani, John Snaith

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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.

Original language	English
Journal	Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology
DOIs	https://doi.org/10.1039/c2pp05320a
Publication status	Published - 17 Jan 2012

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10.1039/c2pp05320a

The Development of Novel Caged Beta-iactum Antibiotics: Tools for the Study of Bacterial Resistance by time-resolved IR spectroscopy
Snaith, J.
Biotechnology & Biological Sciences Research Council
20/10/04 → 19/04/08
Project: Research Councils

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Russell, AG., Sadler, MJ., Laidlaw, HJ., Gutiérrez-Loriente, A., Wharton, C., Carteau, D., Bassani, DM., & Snaith, J. (2012). Photorelease of tyrosine from α-carboxy-6-nitroveratryl (αCNV) derivatives. Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology. https://doi.org/10.1039/c2pp05320a

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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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doi = "10.1039/c2pp05320a",

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Russell, AG, Sadler, MJ, Laidlaw, HJ, Gutiérrez-Loriente, A, Wharton, C, Carteau, D, Bassani, DM & Snaith, J 2012, 'Photorelease of tyrosine from α-carboxy-6-nitroveratryl (αCNV) derivatives.', Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology. https://doi.org/10.1039/c2pp05320a

TY - JOUR

T1 - Photorelease of tyrosine from α-carboxy-6-nitroveratryl (αCNV) derivatives.

AU - Russell, AG

AU - Sadler, MJ

AU - Laidlaw, HJ

AU - Gutiérrez-Loriente, A

AU - Wharton, Christopher

AU - Carteau, D

AU - Bassani, DM

AU - Snaith, John

PY - 2012/1/17

Y1 - 2012/1/17

N2 - 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.

AB - 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.

U2 - 10.1039/c2pp05320a

DO - 10.1039/c2pp05320a

M3 - Article

C2 - 22249211

SN - 1474-9092

JO - Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology

JF - Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology

ER -

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

Abstract

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The Development of Novel Caged Beta-iactum Antibiotics: Tools for the Study of Bacterial Resistance by time-resolved IR spectroscopy

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