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- W2034134107 abstract "The cyclization of 8′-hydroxyabscisic acid to phaseic acid was investigated by feeding RS-[3′,5,7-2D6]abscisic acid to tomato (Lycopersicon esculentum) shoots, the 1′-S-enantiomer was metabolized to dihydrophaseic acid-4′-O-β-d-glucopyranoside (DPAGS) which was isolated as the acetylated methyl ester and subjected to 500 MHz 1H NMR. The 2H atom from C-3′ of abscisic acid (ABA) was confined to the axial 3′-pro-S position of DPAGS (numbered as in ABA) and so the carbanion presumed to be formed at C-3′ during cyclization is protonated from the oxymethylene bridge, β-face. Enolization of the 3′-hydrogen atoms of phaseic acid in D2O at pH 10.55 exchanged the axial hydrogen atom (α-face) preferentially. Thus the carbanion present at this position during cyclization is protonated from the opposite side. This suggests that the reaction that gives rise to phaseic acid is catalysed enzymically." @default.
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- W2034134107 date "1988-01-01" @default.
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- W2034134107 title "The cyclization of 8′-hydroxy abscisic acid to phaseic acid in vivo" @default.
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- W2034134107 doi "https://doi.org/10.1016/0031-9422(88)84088-3" @default.
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