1ST EXAMPLE OF DIASTEREOTOPIC FACE ACTIVATION AND CHIRAL RECOGNITION WITHOUT METAL ASSISTANCE - A NOVEL 5-DEAZAFLAVIN ENZYME MODEL

A chiral 5-deazaflavin 1 with 2-hydroxynaphthyl group at N(3) position of the pyrimidine ring moiety was synthesized. 1 underwent, in the absence of magnesium ion, a ''(net) hydride transfer'' from BNAH to C(5) almost exclusively on the face where OH group is present. It was also...

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Bibliographic Details
Published inTetrahedron letters Vol. 33; no. 47; pp. 7173 - 7176
Main Authors KAWAMOTO, T, TOMISHIMA, M, KUNITOMO, J, YONEDA, F, HAYAMI, J
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 17.11.1992
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
FLAVINOPHANES
FLAVINS
COENZYME MODELS
REDUCTION
NAD(P)H
RACEMIZATION
HYDROGEN TRANSFER
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Summary:A chiral 5-deazaflavin 1 with 2-hydroxynaphthyl group at N(3) position of the pyrimidine ring moiety was synthesized. 1 underwent, in the absence of magnesium ion, a ''(net) hydride transfer'' from BNAH to C(5) almost exclusively on the face where OH group is present. It was also the case with PNPH, and enantioselectivity for PNPH by 1 was higher in the absence of magnesium ion than in its presence. These results indicate that the ''diastereotopic face activation'' in 1 is operated as well as chiral recognition for PNPH by 1.
ISSN:0040-4039
DOI:10.1016/S0040-4039(00)60865-1