Journal of Lipid Research, Vol 19, 187-190, Copyright © 1978 by Lipid Research, Inc.
Absolute configuration of pentahydroxy bile alcohols excreted by patients with cerebrotendinous xanthomatosis: a circular dichroism study
B Dayal, G Salen, GS Tint, V Toome, S Shefer and EH Mosbach
The absolute configurations of the C27 pentahydroxy bile alcohols present
in bile and feces of two patients with cerebrotendinous xanthomatosis (CTX)
were determined by circular dichroism (CD) spectroscopy. The CD spectra of
5beta-cholestane- 3alpha,7alpha,12alpha,24alpha,25-pentol in the presence
of Eu(fod)3 [tris(1,1,1,2,2,3,3-heptafluoro-7,7-dimethyloctane-4,6-dionato)
europium (III)] exhibited a negative Cotton effect and was assigned to 24R
absolute configuration. Conversely, 5beta-cholestane-
3alpha,7alpha,12alpha,24beta,25-pentol showed a strong positive Cotton
effect and was assigned the 24S configuration. These assignments were based
upon comparison with a model compound, 5-cholestene- 3beta,24(R),25-triol,
whose single-crystal X-ray structure has been determined. The importance of
these data is to establish a structural mechanism for the conversion of
5beta-cholestane- 3alpha,7alpha,12alpha,24S,25-pentol rather than
5beta-cholestane- 3alpha,7alpha,12alpha,24R,25-pentol into cholic acid in
man as well as in animals.
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