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Revised stereochemistry of ceramide-trafficking inhibitor HPA-12 by X-ray crystallography analysis
Masaharu Ueno1, Yi-Yong Huang, Akihito Yamano
1Department of Chemistry, School of Science, The University of Tokyo, Hongo, Tokyo 113-0033, Japan.
Abstract:
In response to Berkeš's report revising the stereochemistry of HPA-12, an important ceramide-trafficking inhibitor that was discovered and synthesized and its stereochemistry determined in 2001, the synthesis and the stereochemistry were reinvestigated. A large-scale synthetic method for HPA-12 based on a Zn-catalyzed asymmetric Mannich-type reaction in water was developed. Single crystals of HPA-12 for X-ray crystallographic analysis were obtained from ethyl propionate/n-hexane, and the stereochemistry was definitely determined to be 1R,3S, consistent with Berkeš's revised structure.
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