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Pteridine. Teil LXXXI . Mechanismus der Photooxidation von 5,6‐Dihydro‐1,3‐dimethyl‐6‐thioxopteridin‐2,4(1 H ,3 H )‐dion
Author(s) -
Heckel Armin,
Pfleiderer Wolfgang
Publication year - 1986
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.19860690516
Subject(s) - chemistry , singlet oxygen , superoxide , pteridine , autoxidation , photochemistry , medicinal chemistry , reaction mechanism , oxygen , ion , stereochemistry , catalysis , organic chemistry , enzyme
Mechanism of the Photooxidation of 5,6‐Dihydro‐1,3‐dimethyl‐6‐thioxopteridine‐2,4(1 H ,3 H )‐dione The mechanism of the photooxidation of 5,6‐dihydro‐1,3‐dimethyl‐6‐thioxopteridine‐2,4(1 H ,3 H )‐dione ( 9 ) has been investigated in dependence of the pH. Photooxidation of the anion species in weak alkaline solution takes place by singlet oxygen as well as the superoxide radical anion forming 1,2,3,4‐tetrahydro‐1,3‐dimethyl‐2,4‐dioxopteridine‐6‐sulfinate ( 5 ) as the first detectable reaction product. In acidic medium, a more complex photooxidation process is observed leading, in a radical‐chain mechanism, to 6,6′‐dithiobis[1,3‐dimethylpteridine‐2,4(1 H ,3 H )‐dione] ( 6 ).