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Reduktive Photoalkylierung des Flavinkerns und Flavinkatalysierte Photodecarboxylierung von Phenylacetat Studien in der Flavinreihe. 15. Mitteilung [1]
Author(s) -
Walker W. H.,
Hemmerich P.,
Massey V.
Publication year - 1967
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19670500812
Subject(s) - chemistry , phenylacetate , flavin group , residue (chemistry) , ion , nitrogen , stereochemistry , medicinal chemistry , organic chemistry , biochemistry , enzyme
Structure and properties of leucoflavin derivatives obtained through flavinsensitized photodecarboxylation of phenylacetate ions are described. The photoreduction of flavin with phenylacetate as donor is shown to be a quantitative photoalkylation, the benzyl residue entering either position 5 (nitrogen) or the bridge position 4a (carbon) of the flavin nucleus, depending on the conditions. The isomers were isolated, and identified by IR., NMR., and elementary analysis. The benzyl residue migrates from N(5) to C(4a) upon heating.