Literature DB >> 16395435

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

Andreas Barth1, Stephen R Martin, John E T Corrie.   

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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Year:  2005        PMID: 16395435     DOI: 10.1039/b515469c

Source DB:  PubMed          Journal:  Photochem Photobiol Sci        ISSN: 1474-905X            Impact factor:   3.982


  4 in total

Review 1.  Photoremovable protecting groups in chemistry and biology: reaction mechanisms and efficacy.

Authors:  Petr Klán; Tomáš Šolomek; Christian G Bochet; Aurélien Blanc; Richard Givens; Marina Rubina; Vladimir Popik; Alexey Kostikov; Jakob Wirz
Journal:  Chem Rev       Date:  2012-12-21       Impact factor: 60.622

2.  Photo-cleavable analog of BAPTA for the fast and efficient release of Ca2.

Authors:  Mariia V Sutton; Matthew McKinley; Revathy Kulasekharan; Vladimir V Popik
Journal:  Chem Commun (Camb)       Date:  2017-05-18       Impact factor: 6.222

3.  Synthesis and Photolytic Assessment of Nitroindolinyl-Caged Calcium Ion Chelators.

Authors:  George Papageorgiou; John E T Corrie
Journal:  Molecules       Date:  2022-04-20       Impact factor: 4.927

4.  Optically switchable chelates: optical control and sensing of metal ions.

Authors:  Tomoyo Sakata; David K Jackson; Shu Mao; Gerard Marriott
Journal:  J Org Chem       Date:  2007-12-12       Impact factor: 4.354

  4 in total

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