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• W1492795272 abstract "Abstract Structures and reactivities of 5-deazaflavins were studied by using new 5-deazaflavinophanes dFl( n ) in which N(3) and O(2′) in the 10-(2-hydroxy)phenyl group were linked by a (CH 2 ) n chain ( n = 8 and 12). dFl(Bu), having n -butyl groups at N(3) and O(2′), was used as a reference. X-ray crystallographic and 1 H NMR studies established that in the Grignard reaction with MeMgBr to yield dFlMe red ( n ) the methyl group attacks the isoalloxazine plane from the axial side and is fixed at the axial position. In NaBH 4 reduction of dFlMe( n ) to yield dFlMe red ( n ) hydride attacks the isoalloxazine plane from the axial side, but the 5-methyl group is displaced from “equatorial” to “axial” by ring inversion in order to minimize steric hindrance. The axial preference observed for nucleophilic attacks is explained by a stereoelectronic effect. dFlMe red ( n ), having only H eq at the C(5)-position, was much less reactive as reductant than dFl red ( n ) having both H eq and H ax . The deactivation is rationalized by such that (i) more reactive H ax is lost by substitution with the methyl group and (ii) remaining H eq , surrounded by bulky groups, behaves as a less reactive “buried hydride equivalent”. These novei structure-reactivity relationships have important implications on biochemical studies of flavoenzymes." @default.
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• W1492795272 date "1989-09-01" @default.
• W1492795272 modified "2023-09-27" @default.
• W1492795272 title "Coenzyme models 51" @default.
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• W1492795272 doi "https://doi.org/10.1016/0045-2068(89)90036-9" @default.
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