What Is the True Structure of D609, a Widely Used Lipid Related Enzyme Inhibitor?

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, an...

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Bibliographic Details
Published in:Organic letters 2016-02, Vol.18 (4), p.768-771
Main Authors: Kato, Mikako, Hammam, Mostafa A. S, Taniguchi, Tohru, Suga, Yoshiko, Monde, Kenji
Format: Article
Language:English
Subjects:
Bridged-Ring Compounds - chemistry
Bridged-Ring Compounds - pharmacology
Circular Dichroism
Enzyme Inhibitors - chemistry
Enzyme Inhibitors - pharmacology
Lipids - chemistry
Molecular Structure
Stereoisomerism
Thiones - chemistry
Thiones - pharmacology
Type C Phospholipases - antagonists & inhibitors
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.6b00025