5-deazaflavin Derivatives Research Articles

ChemInform Abstract: Synthesis and Reaction of a New Type of 5-Deazaflavin with Axial and Planar Chirality.

Abstract A new type of 5-deazaflavin derivative with axial and planar chirality was synthesized as a flavoenzyme model. A novel optical resolution gave an enantiomeric pair of the 5-deazaflavins 1a,b. Compounds1a,b were optically stable and effectively discriminated PNPH enantiomers in a model reaction of intercoenzyme hydrogen transfer.

Asymmetric reduction with 5-deazaflavin. II. Synthesis of some chiral 5-deazaflavin derivatives.

For the purpose of development of functional biomimetic coenzyme models, we prepared some new types of chiral 5-deazaflavin derivatives. Syntheses of 5-deazaflavin derivatives possessing a chiral substituent at the C(6) position, and a chiral tertiary asymmetric carbon center at C(5) were achieved in rather satisfactory yield

A new synthetic approach to 5-deazaflavin and 5-deaza-10-thiaflavin.

A novel, one-step synthesis of 5-deazaflavin developed, in which a [4+2]cycloaddition is presumably involved, to give the 5-deazaflavin derivative in moderate yield. This methodology was successfully applied to the stepwise preparation of its thio analogue, 5-deaza-10-thiaflavin, whose 1, 5-dihydro derivative was transformed into the corresponding sulfone in good yield.

Synthesis and reaction of a new type of 5-deazaflavin with axial and planar chirality

A new type of 5-deazaflavin derivative with axial and planar chirality was synthesized as a flavoenzyme model. A novel optical resolution gave an enantiomeric pair of the 5-deazaflavins 1a,b. Compounds 1a,b were optically stable and effectively discriminated PNPH enantiomers in a model reaction of intercoenzyme hydrogen transfer.

Synthesis of chiral 5-deazaflavin derivatives and their use in asymmetric reduction of ethyl benzoylformate.

Some 1, 5-dihydro-5-deazaflavin (1, 5-dihydropyrimido [4, 5-b] quinoline-2, 4 (3H, 10H) -dione) derivatives possessing chiral substituents at the N-3 position were synthesized. Asymmetric reduction of ethyl benzoylformate in the presence of magnesium perchlorate was carried out with these chiral 1, 5-dihydro-5-deazaflavin derivatives to give ethyl mandelate in moderate optical and chemical yield. The influence of metal additives other than magnesium upon the asymmetric induction and yield of the reduction was investigated, and it was suggested that intermediate ternary complexation is probably involved in the reaction. No improvement of chiral induction was obtained by changing the metal catalyst.

The inhibition of the photochemical dimerization of 1,3-dimethylthymine by flavin and 5-deazaflavin derivatives.

We studied the effect of several falvin and 5-deazaflavin derivatives (flavin dyes) on the photochemical dimerization of 1.3-dimethylthymine as a model compound of DNA.These flavin dyes, especially those with the D-ribityl moiety such as riboflavin, 5-deazariboflavin and F420 chromophore, had a great inhibitory effect on 1, 3-dimethylthymine photodimerization. But they did not detectably catalyze dimer cleavage at physiological pH levels.

Preparation of chiral 5-deazaflavin derivatives and their asymmetric reduction of ethyl benzoylformate

1,5-Dihydro-5-deazaflavin derivatives possessing a chiral substituent at N(3) position were synthesized, with which moderate asymmetric induction was observed in the reduction of ethyl benzoylformate.