title: Expedient and practical synthesis of CERT-dependent ceramide trafficking inhibitor HPA-12 and its analogues.
abstract: The practical stereodivergent route to both syn- and anti-diastereomers of 1-substituted 3-aminobutane-1,4-diols based on the crystallization-induced asymmetric transformation (CIAT) approach was completed. This led to the revision of the reported stereochemistry of the first inhibitor of CERT-dependent ceramide trafficking HPA-12 from (R,R)-anti- to the (R,S)-syn-enantiomer. Due to the expeditiousness of production and inexpensive conditions developed, a series of alkyl- and aryl-substituted analogues of HPA-12 is also reported.
authors.affiliation: Department of Organic Chemistry, Slovak University of Technology, Radlinského 9, 81237 Bratislava, Slovakia.
authors.forename: Andrej
authors.initials: A
authors.lastname: Ďuriš
authors.forename: Tomáš
authors.initials: T
authors.lastname: Wiesenganger
authors.forename: Daniela
authors.initials: D
authors.lastname: Moravčíková
authors.forename: Peter
authors.initials: P
authors.lastname: Baran
authors.forename: Jozef
authors.initials: J
authors.lastname: Kožíšek
authors.forename: Adam
authors.initials: A
authors.lastname: Daïch
authors.forename: Dušan
authors.initials: D
authors.lastname: Berkeš
mesh_terms: D000577:Amides / Q000138:chemical synthesis* / Q000494:pharmacology; D002518:Ceramides / Q000378:metabolism; D008958:Models, Molecular; D015394:Molecular Structure; D017346:Protein Serine-Threonine Kinases / Q000037:antagonists & inhibitors* / Q000378:metabolism; D013237:Stereoisomerism
chemical_list: D000577:Amides; D002518:Ceramides; C441643:N-(3-hydroxy-1-hydroxymethyl-3-phenylpropyl)dodecanamide; D017346:Protein Serine-Threonine Kinases