Studies in the Flavin Series. Part XVII.

Ghisla, Sandro; Hemmerich, Peter; Jefcoate, C.

Studies in the Flavin Series. Part XVII.

Files

J_Chem_Soc_Perkin_Trans_I_1972_GhislaStudies_in_the_flavin_serie.pdf(1.49 MB)

Date

1972

Authors

Ghisla, Sandro

Hemmerich, Peter

Jefcoate, C.

Publication type

Journal article

Published in

Journal of the Chemical Society / Perkin transactions I ; 1972. - pp. 1564-1569

Abstract

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.

Subject (DDC)

570 Biosciences, Biology

Cite This

ISO 690

GHISLA, Sandro, Peter HEMMERICH, C. JEFCOATE, 1972. Studies in the Flavin Series. Part XVII.. In: Journal of the Chemical Society / Perkin transactions I, pp. 1564-1569

BibTex

@article{Ghisla1972Studi-8600,
  year={1972},
  title={Studies in the Flavin Series. Part XVII.},
  journal={Journal of the Chemical Society / Perkin transactions I},
  pages={1564--1569},
  author={Ghisla, Sandro and Hemmerich, Peter and Jefcoate, C.}
}

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