Stereochemistry of the reduction of 24-ethyldesmosterol to sitosterol in tissue cultures of Oryza sativa.
Feeding of [26-13C]- and [27-13C]-24-ethyldesmosterols to cultured cells of Oryza sativa followed by 13C-NMR analysis of the biosynthesized sitosterol revealed that the reduction of 24(25)-double bond proceeds with an anti-addition of hydrogen atoms, thus the E-methyl group of the olefinic precursor becomes the pro-S-methyl on C-25 of sitosterol.
Fujimoto
Y
Y
Department of Chemistry, Tokyo Institute of Technology, Japan.
Sato
N
N
Okuzumi
T
T
Yamada
J
J
Morisaki
M
M
D002849:Chromatography, Gas; D002851:Chromatography, High Pressure Liquid; D046508:Culture Techniques; D003897:Desmosterol / Q000031:analogs & derivatives* / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D012275:Oryza; D010084:Oxidation-Reduction; D012855:Sitosterols / Q000378:metabolism*; D013237:Stereoisomerism
C116730:24-ethyldesmosterol; D012855:Sitosterols; D003897:Desmosterol; C025473:gamma-sitosterol