title: What Is the True Structure of D609, a Widely Used Lipid Related Enzyme Inhibitor?
abstract: D609 (1) has been used as a lipid-related enzyme inhibitor during the past three decades. Although it has eight possible stereoisomers, no systematic research considering its chirality has been performed. In this paper, eight possible chiral alcohols as direct precursors of D609 were synthesized, and their stereochemistries were elucidated by a vibrational circular dichroism (VCD) technique. Phosphatidylcholine-specific phospholipase C and sphingomyelin synthase inhibition assays of these isomers showed considerable differences in their activities.
authors: Graduate School of Life Science and ‡Faculty of Advanced Life Science, Frontier Research Center for Post-Genome Science and Technology, Hokkaido University , Kita 21 Nishi 11, Sapporo 001-0021, Japan.
authors: Mikako
authors: M
authors: Kato
authors: Graduate School of Life Science and ‡Faculty of Advanced Life Science, Frontier Research Center for Post-Genome Science and Technology, Hokkaido University , Kita 21 Nishi 11, Sapporo 001-0021, Japan.
authors: Mostafa A S
authors: MA
authors: Hammam
authors: Graduate School of Life Science and ‡Faculty of Advanced Life Science, Frontier Research Center for Post-Genome Science and Technology, Hokkaido University , Kita 21 Nishi 11, Sapporo 001-0021, Japan.
authors: Tohru
authors: T
authors: Taniguchi
authors: Graduate School of Life Science and ‡Faculty of Advanced Life Science, Frontier Research Center for Post-Genome Science and Technology, Hokkaido University , Kita 21 Nishi 11, Sapporo 001-0021, Japan.
authors: Yoshiko
authors: Y
authors: Suga
authors: Graduate School of Life Science and ‡Faculty of Advanced Life Science, Frontier Research Center for Post-Genome Science and Technology, Hokkaido University , Kita 21 Nishi 11, Sapporo 001-0021, Japan.
authors: Kenji
authors: K
authors: Monde
mesh_terms: D001952:Bridged-Ring Compounds / Q000737:chemistry* / Q000494:pharmacology*; D002942:Circular Dichroism; D004791:Enzyme Inhibitors / Q000737:chemistry* / Q000494:pharmacology*; D008055:Lipids / Q000737:chemistry; D015394:Molecular Structure; D009636:Norbornanes; D013237:Stereoisomerism; D013859:Thiocarbamates; D013871:Thiones / Q000737:chemistry* / Q000494:pharmacology*; D010738:Type C Phospholipases / Q000037:antagonists & inhibitors*
chemical_list: D001952:Bridged-Ring Compounds; D004791:Enzyme Inhibitors; D008055:Lipids; D009636:Norbornanes; D013859:Thiocarbamates; D013871:Thiones; C046498:tricyclodecane-9-yl-xanthogenate; D010738:Type C Phospholipases; C105598:phosphatidylcholine-specific phospholipase C