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Barth A, Martin SR, Corrie JE. Decarboxylation is a significant reaction pathway for photolabile calcium chelators and related compounds. Photochem Photobiol Sci. 2005;5(1):107-15doi: 10.1039/b515469c.
Barth, A., Martin, S. R., & Corrie, J. E. (2006). Decarboxylation is a significant reaction pathway for photolabile calcium chelators and related compounds. Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology, 5(1), 107-15. https://doi.org/10.1039/b515469c
Barth, Andreas, et al. "Decarboxylation is a significant reaction pathway for photolabile calcium chelators and related compounds." Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology vol. 5,1 (2006): 107-15. doi: https://doi.org/10.1039/b515469c
Barth A, Martin SR, Corrie JE. Decarboxylation is a significant reaction pathway for photolabile calcium chelators and related compounds. Photochem Photobiol Sci. 2006 Jan;5(1):107-15. doi: 10.1039/b515469c. Epub 2005 Dec 01. PMID: 16395435.
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Photochem Photobiol Sci. 2006 Jan;5(1):107-15. doi: 10.1039/b515469c. Epub 2005 Dec 01.

Decarboxylation is a significant reaction pathway for photolabile calcium chelators and related compounds.

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

Andreas Barth, Stephen R Martin, John E T Corrie

Affiliations

  1. Department of Biochemistry and Biophysics, Arrhenius Laboratories for Natural Sciences, Stockholm University, SE-106 91, Stockholm, Sweden.

PMID: 16395435 DOI: 10.1039/b515469c

Abstract

Photolysis of amino acids that bear a 2-nitrobenzyl protecting group on the amino nitrogen involves a normal 2-nitrobenzyl-type photocleavage to release the amino acid but also a second mechanistic pathway, that appears to be initiated by single electron transfer from the amino group to the excited state of the nitroaromatic. The end result of this pathway is photodecarboxylation. Quantitative experiments suggest that this latter pathway can contribute between 10 and 80% of the total reaction flux in different compounds. It appears that the aminium radical, the first product of the single electron transfer, can be intercepted by certain amino acids, resulting in a transfer of decarboxylation to this "sacrificial" amino acid. Possible implications for precise details of calcium release from photolabile derivatives of EDTA and EGTA are discussed.

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