Non-stereoselective formation of 3 alpha,7 alpha,12 alpha,24-tetrahydroxy-5 beta-cholestan-26-oic acid during cholic acid biosynthesis.
Incubation of (25RS)-, (25R)- and (25S)-3 alpha,7 alpha,12 alpha-trihydroxy-5 beta-cholestan-26-oic acid (THCA, 6, 6a, 6b) and (24E)-3 alpha,7 alpha,12 alpha-trihydroxy-5 beta-cholest-24-en-26-oic acid (7) with rat liver mitochondria gave all four stereoisomers (9a,9b,9c,9d) of 3 alpha,7 alpha,12 alpha,24-Tetrahydroxy-5 beta-cholestan-26-oic acid (TeHCA). The corresponding 27-nor analogs (10,11) were also converted non-stereoselectively to a 1:1 mixture of the epimeric 24-hydroxy compounds (12).
Kobayashi
N
N
Kyoritsu College of Pharmacy, Tokyo, Japan.
Hagiwara
C
C
Morisaki
M
M
Yuri
M
M
Oya
I
I
Fujimoto
Y
Y
D000818:Animals; D002777:Cholestanols / Q000378:metabolism*; D002784:Cholesterol / Q000031:analogs & derivatives / Q000378:metabolism; D019826:Cholic Acid; D002793:Cholic Acids / Q000096:biosynthesis*; D002851:Chromatography, High Pressure Liquid; D008401:Gas Chromatography-Mass Spectrometry; D008297:Male; D008930:Mitochondria, Liver / Q000378:metabolism*; D051381:Rats; D017208:Rats, Wistar; D013237:Stereoisomerism
D002777:Cholestanols; D002793:Cholic Acids; C024759:3,7,12,24-tetrahydroxycholestanoic acid; C059108:3,7,12-trihydroxycholest-24-enoic acid; C022069:3,7,12-trihydroxycholestan-26-oic acid; D002784:Cholesterol; D019826:Cholic Acid