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- W2014298577 abstract "Acyloin has been proposed to be an intermediate in the biosynthesis of long chain alkane-2,3-diols. In order to test this possibility, specifically labeled 3-hydroxyoctadecane-2-one (acyloin) was synthesized by coupling 2-methyl-1,3-dithiane with [1-14C]hexadecanal followed by cleaving of the thioketal. Injection of the synthetic 3-hydroxy [3-14C]octadecane-2-one into the uropygial gland of the ring-necked pheasant resulted in the formation of labeled octadecane-2,3-diol. Chemical degradation of this diol showed that all of the 14C was contained in C-3 of the diol showing direct conversion of acyloin to the diol. These observations support the hypothesis that alkane-2,3-diols might be biosynthesized by reduction of the acyloin derived from a condensation between hydroxyethyl thiamine pyrophosphate and fatty aldehyde. Gas-liquid chromatographic analysis of the alkane-2,3-diols, as their isopropylidene derivatives, of the pheasant strongly suggests that they are of the erythro-configuration; however, alkane-2,3-diol enzymatically formed from the racemic acyloin injected into the gland contained 59.5% erythro- and 40.5% threo-diastereoisomers. This distribution was identical to that produced by chemical reduction of the synthetic racemic acyloin. These results clearly show that the reduction step does not show a preference for either of the enantiomers of the acyloin and that the stereospecificity in diol biosynthesis probably resides in the condensation step." @default.
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- W2014298577 date "1975-11-01" @default.
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- W2014298577 title "Biosynthesis of alkane-2,3-diols: Chemical synthesis of 3-hydroxy-[3-14C] octadecane-2-one and its reduction to [3-14C]octadecane-2,3-diol in the uropygial glands of ring-necked pheasants (Phasianus colchicus)" @default.
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- W2014298577 doi "https://doi.org/10.1016/0003-9861(75)90033-8" @default.
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