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Synthesis of rigidified flavin-guanidinium ion conjugates and investigation of their photocatalytic properties.

ABSTRACT: Flavin chromophores can mediate redox reactions upon irradiation by blue light. In an attempt to increase their catalytic efficacy, flavin derivatives bearing a guanidinium ion as oxoanion binding site were prepared. Chromophore and substrate binding site are linked by a rigid Kemp's acid structure. The molecular structure of the new flavins was confirmed by an X-ray structure analysis and their photocatalytic activity was investigated in benzyl ester cleavage, nitroarene reduction and a Diels-Alder reaction. The modified flavins photocatalyze the reactions, but the introduced substrate binding site does not enhance their performance.

SUBMITTER: Schmaderer H

PROVIDER: S-EPMC2707025 | biostudies-literature | 2009 May

REPOSITORIES: biostudies-literature

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Synthesis of rigidified flavin-guanidinium ion conjugates and investigation of their photocatalytic properties.

Schmaderer Harald H Bhuyan Mouchumi M König Burkhard B

Beilstein journal of organic chemistry 20090528

Flavin chromophores can mediate redox reactions upon irradiation by blue light. In an attempt to increase their catalytic efficacy, flavin derivatives bearing a guanidinium ion as oxoanion binding site were prepared. Chromophore and substrate binding site are linked by a rigid Kemp's acid structure. The molecular structure of the new flavins was confirmed by an X-ray structure analysis and their photocatalytic activity was investigated in benzyl ester cleavage, nitroarene reduction and a Diels-A ...[more]

PMID: 19590745

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