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Photochemistry and thermal decarboxylation of alpha-phosphoryloxy-p-nitrophenylacetates
Stockholm University, Faculty of Science, Department of Biochemistry and Biophysics.
Stockholm University, Faculty of Science, Department of Biochemistry and Biophysics.
2009 (English)In: Photochemistry and Photobiology, ISSN 0031-8655, E-ISSN 1751-1097, Vol. 85, 1089-1096 p.Article in journal (Refereed) Published
Abstract [en]

α-Carboxy-4-nitrobenzyl phosphate 4 and its derived monomethyl phosphate ester 5 were synthesized and purified by anion-exchange chromatography. A gradient of LiCl was necessary for elution of the anion-exchange column to avoid unexpected thermal decarboxylation that occurred during vacuum evaporation when the volatile triethylammonium bicarbonate buffer was used. Photolysis of each compound was accompanied by decarboxylation, and 4 released inorganic phosphate with near-100% stoichiometry. Time-resolved infrared spectroscopy of the photolysis reaction, coupled with density functional theory calculations of vibrational frequencies, enabled us to infer a mechanism for the photolytic pathway, although there was some evidence for a second pathway also being operative. In contrast to the results for 4, photolysis of 5 appeared to release little or no monomethyl phosphate.

Place, publisher, year, edition, pages
2009. Vol. 85, 1089-1096 p.
Keyword [en]
α-Carboxy-4-nitrobenzyl phosphate, 4, α-Carboxy-4-nitrobenzyl methyl phosphate, 5, 4-Nitrobenzyl methyl phosphate, 13
National Category
Natural Sciences
Research subject
URN: urn:nbn:se:su:diva-33338DOI: 10.1111/j.1751-1097.2009.00576.xISI: 000269463700005OAI: diva2:283021
Available from: 2009-12-22 Created: 2009-12-22 Last updated: 2011-06-15Bibliographically approved

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Rudbeck, MariaBarth, Andreas
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