J. Lipid Res.
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Journal of Lipid Research, Vol 27, 393-397, Copyright © 1986 by Lipid Research, Inc.

ARTICLES

Absolute configuration at C-24 of 5 beta-ranol, a principal bile alcohol of the bullfrog

K Kihira, Y Noma, K Tsuda, T Watanabe, Y Yamamoto, M Une and T Hoshita

The stereochemistry of the hydroxyl group at C-24 in 5 beta-ranol (27- nor-5 beta-cholestane-3 alpha,7 alpha,12 alpha,24,26-pentol) a principal bile alcohol of the bullfrog which is structurally related to the major human urinary bile alcohol, 27-nor-5 beta-cholestane-3 alpha,7 alpha,12 alpha,24,25-pentol, is described. Two isomers (IIIa and IIIb) at C-24 of 27-nor-5 beta-cholest-25-ene-3 alpha,7 alpha,12 alpha, 24-tetrol were synthesized from cholic acid (I) by the conversion to 3 alpha, 7 alpha, 12 alpha-triacetoxy-5 beta-cholan-24-al (II) followed by a Grignard reaction with vinylmagnesium bromide. The absolute configurations at C-24 of the unsaturated tetrols (IIIa and IIIb) were elucidated as S and R, respectively, by means of the difference of the reactivity to Sharpless oxidation, a stereoselective epoxidation. Catalytic hydrogenation of each delta 25-tetrol (IIIa or IIIb) gave (24R)- or (24S)-27-nor-5 beta-cholestane-3 alpha,7 alpha,12 alpha, 24-tetrol (IVa or IVb). The configurations at C-24 of two isomeric 3 alpha,7 alpha,12 alpha,24-tetrahydroxy-27-nor-5 beta- cholestan-26-oic acids (Va and Vb) were determined as S and R, respectively, by means of their conversion into the saturated tetrols (IVa and IVb) of known absolute configurations by a Kolbe electrolytic coupling with acetic acid. The lithium aluminum hydride reduction product of the 24R-acid (Vb) was identical with the naturally occurring 5 beta-ranol, hence 5 beta-ranol has the 24R configuration.
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M. Une, S. Takenaka, T. Kuramoto, K. Fujimura, T. Hoshita, and K. Kihira
Structural and biosynthetic studies of a principal bile alcohol, 27-nor-5{beta}-cholestane-3{alpha},7{alpha},12{alpha},24,25-pentol, in human urine
J. Lipid Res., October 1, 2000; 41(10): 1562 - 1567.
[Abstract] [Full Text]


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Copyright © 1986 by the American Society for Biochemistry and Molecular Biology.