Stereochemical fate of C-26 and C-27 during the conversion of isofucosterol to sitosterol and of 24-methylenecholesterol to campesterol and dihydrobrassicasterol in Oryza sativa cell cultures.
Administration of pro-R-methyl-13C-labeled isofucosterol to cultured cells of Oryza sativa revealed that the pro-R and pro-S methyls at C-25 become the pro-R and pro-S methyls at C-25 of sitosterol, respectively. Similar administration experiments using pro-S-methyl-13C-labeled 24-methylenecholesterol established that the pro-R and pro-S methyls at C-25 of 24-methylenecholesterol become the pro-R and pro-S methyls of campesterol, and the pro-S and pro-R methyls of dihydrobrassicasterol, respectively. These results are compatible with our recently proposed 'syn-SE2' mechanism' for double bond isomerization of delta 24(28) into delta 24(25).
Nasu
K
K
Kyoritsu College of Pharmacy, Tokyo, Japan.
Takahashi
K
K
Morisaki
M
M
Fujimoto
Y
Y
D002478:Cells, Cultured; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D012275:Oryza / Q000737:chemistry* / Q000166:cytology; D013237:Stereoisomerism; D013261:Sterols / Q000737:chemistry*
D013261:Sterols