First Chemical Synthesis, Aggregation Behavior and Cholesterol Solubilization Properties of Pythocholic Acid and 16α-Hydroxycholic Acid

Nonappa, * and Maitra, Uday (2007) First Chemical Synthesis, Aggregation Behavior and Cholesterol Solubilization Properties of Pythocholic Acid and 16α-Hydroxycholic Acid. In: European Journal of Organic Chemistry, 2007 (20). pp. 3331-3336.

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Abstract

The first chemical synthesis of pythocholic acid, a major component of python’s bile, and $3\alpha$,$7\alpha$,$12\alpha$,$16\alpha$-tetrahydroxy-$5\beta$-cholan-24-oic acid ($16\alpha$-hydroxycholic acid), a minor component in Shoebill stork’s bile, was achieved starting from readily available cholic acid in overall yields of 5% and 5.5%, respectively, through a common intermediate. A biomimetic template-directed remote functionalization strategy was utilized to selectively functionalize C-16 of the steroid skeleton. This synthesis involves a series of regio and chemoselective transformations. Pythocholic acid showed unusually low critical micellar concentration (CMC) with high cholesterol solubilization ability.

Item Type:	Journal Article
Publication:	European Journal of Organic Chemistry
Publisher:	John Wiley & Sons, Inc.
Additional Information:	Copyright of this article belongs to John Wiley & Sons, Inc.
Keywords:	Pythocholic acid;Oxidation;Critical micellar concentration;Regio and chemoselective;Remote functionalization
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	10 Jun 2008
Last Modified:	19 Sep 2010 04:45
URI:	http://eprints.iisc.ac.in/id/eprint/14249

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