Publikation: Studies in the Flavin Series. Part XVII.
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1972
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Journal of the Chemical Society / Perkin transactions I, pp. 1564-1569
Zusammenfassung
The distribution of products from the reductive alkylation of 1,3.7,8-tetramethylalloxazinde epends upon whether saturated (hard) or unsaturated (soft) alkylating agents are used. The former yield 5-alkylated 5.1 O-dihydroalloxazines and, under more drastic conditions, 5.5-dialkylated derivatves, while the latter (benzyl and allyl bromide) yield 4a-monoalkylated and 4a,5-dialkylated derivatives. The 5-alkyldihydroalloxazines are readily oxidised to the 5-alkylalloxaziniurn salts, which either undergo hydrolytic dealkylation to the initial alloxazine or, if the 5-substituent is allyl or benzyl, in part rearrange to a 6-alkylalloxazine. Oxygen, under acidic conditions, converts 4a-benzyl- (or al1yl)-dihydroalloxazines into the 6-benzyl- (or allyl-)alloxazine via the 5-substituted alloxazinium salt. The mechanisms of these reactions are discussed and their relevance to group transfer reactions of flavocoenzyrnes is stressed.
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570 Biowissenschaften, Biologie
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GHISLA, Sandro, Peter HEMMERICH, C. JEFCOATE, 1972. Studies in the Flavin Series. Part XVII.. In: Journal of the Chemical Society / Perkin transactions I, pp. 1564-1569BibTex
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<dc:contributor>Hemmerich, Peter</dc:contributor>
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<dcterms:abstract xml:lang="eng">The distribution of products from the reductive alkylation of 1,3.7,8-tetramethylalloxazinde epends upon whether saturated (hard) or unsaturated (soft) alkylating agents are used. The former yield 5-alkylated 5.1 O-dihydroalloxazines and, under more drastic conditions, 5.5-dialkylated derivatves, while the latter (benzyl and allyl bromide) yield 4a-monoalkylated and 4a,5-dialkylated derivatives. The 5-alkyldihydroalloxazines are readily oxidised to the 5-alkylalloxaziniurn salts, which either undergo hydrolytic dealkylation to the initial alloxazine or, if the 5-substituent is allyl or benzyl, in part rearrange to a 6-alkylalloxazine. Oxygen, under acidic conditions, converts 4a-benzyl- (or al1yl)-dihydroalloxazines into the 6-benzyl- (or allyl-)alloxazine via the 5-substituted alloxazinium salt. The mechanisms of these reactions are discussed and their relevance to group transfer reactions of flavocoenzyrnes is stressed.</dcterms:abstract>
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