Revised stereochemistry of ceramide-trafficking inhibitor HPA-12 by X-ray crystallography analysis

Org Lett. 2013 Jun 7;15(11):2869-71. doi: 10.1021/ol401101u. Epub 2013 May 23.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / analysis*
  • Amides / chemical synthesis*
  • Amides / chemistry*
  • Catalysis
  • Ceramides / antagonists & inhibitors*
  • Ceramides / chemistry*
  • Crystallography, X-Ray
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Molecular Structure
  • Stereoisomerism
  • Zinc / chemistry

Substances

  • Amides
  • Ceramides
  • N-(3-hydroxy-1-hydroxymethyl-3-phenylpropyl)dodecanamide
  • Zinc