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Studies of decarboxylation in photolysis of alpha-carboxy-2-nitrobenzyl (CNB) caged compounds.
Stockholm University, Faculty of Science, Department of Biochemistry and Biophysics.
2008 (English)In: Photochem Photobiol Sci, ISSN 1474-905X, Vol. 7, no 1, 84-97 p.Article in journal (Refereed) Published
Abstract [en]

Photolysis of alpha-carboxy-2-nitrobenzyl (CNB) caged compounds, studied here by time-resolved IR and UV spectroscopy, involves at least two pathways. In one, a conventional 2-nitrobenzyl type rearrangement takes place to release the photoprotected species via rapid decay of an aci-nitro intermediate. The alpha-carboxylate moiety of the CNB group is retained and the final by-product from this pathway is 2-nitrosophenylglyoxylate. Direct measurements of product formation confirmed that release via this pathway is faster for CNB-caged compounds than for related caged compounds without an alpha-carboxylate substituent and a rationale for the faster release rate is proposed. In a second pathway, photodecarboxylation of the starting material occurs: this pathway leads only to a slow, minor release of the photoprotected species. The extent to which the latter pathway contributes is affected by the nature of buffer salts in the irradiated solution. It was more prominent in an amine-based buffer (MOPS) than in phosphate buffer.

Place, publisher, year, edition, pages
2008. Vol. 7, no 1, 84-97 p.
Keyword [en]
Carbon Dioxide/chemistry, Carboxylic Acids/*chemistry, Decarboxylation, Hydrogen-Ion Concentration, Kinetics, Molecular Structure, Nitrobenzenes/*chemistry, Photolysis, Spectrophotometry
Identifiers
URN: urn:nbn:se:su:diva-14853ISI: 000252048700011PubMedID: 18167601OAI: oai:DiVA.org:su-14853DiVA: diva2:181373
Available from: 2008-11-05 Created: 2008-11-05 Last updated: 2011-01-10Bibliographically approved

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