title: Revised stereochemistry of ceramide-trafficking inhibitor HPA-12 by X-ray crystallography analysis.
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.
authors.affiliation: Department of Chemistry, School of Science, The University of Tokyo, Hongo, Tokyo 113-0033, Japan.
authors.forename: Masaharu
authors.initials: M
authors.lastname: Ueno
authors.forename: Yi-Yong
authors.initials: YY
authors.lastname: Huang
authors.forename: Akihito
authors.initials: A
authors.lastname: Yamano
authors.forename: Shū
authors.initials: S
authors.lastname: Kobayashi
mesh_terms: D000577:Amides / Q000032:analysis* / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D002518:Ceramides / Q000037:antagonists & inhibitors* / Q000737:chemistry*; D018360:Crystallography, X-Ray; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism; D015032:Zinc / Q000737:chemistry
chemical_list: D000577:Amides; D002518:Ceramides; C441643:N-(3-hydroxy-1-hydroxymethyl-3-phenylpropyl)dodecanamide; D015032:Zinc