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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Veröffentlicht in:	Organic letters 2016-02, Vol.18 (4), p.768-771
Hauptverfasser:	Kato, Mikako, Hammam, Mostafa A. S, Taniguchi, Tohru, Suga, Yoshiko, Monde, Kenji
Format:	Artikel
Sprache:	eng
Schlagworte:	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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Beschreibung
Zusammenfassung:	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