The inhibitory mechanism of bovine pancreatic phospholipase A(2) by aldehyde terpenoids

Citation
K. Tanaka et al., The inhibitory mechanism of bovine pancreatic phospholipase A(2) by aldehyde terpenoids, TETRAHEDRON, 55(6), 1999, pp. 1657-1686
Citations number
51
Language
INGLESE
art.tipo
Article
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
0040-4020 → ACNP
Volume
55
Issue
6
Year of publication
1999
Pages
1657 - 1686
Database
ISI
SICI code
0040-4020(19990205)55:6<1657:TIMOBP>2.0.ZU;2-S
Abstract
We established the stereoselective synthesis of (E)-3-methoxycarbonyl-2,4,6 -trienal compound A and discovered that the compound A showed more powerful inhibitory activity toward phospholipase A(2)(PLA(2)) from bovine pancreas than manoalide which is a typical PLA(2) inhibitor. As the inhibitory mech anism of PLA(2) by A, the irreversible formation of dihydropyridine derivat ive resulting from the reaction of A with lysine residues in PLA(2) was pro posed based on the model reactions. Furthermore, A was found to selectively modify Lys56 which is included in the interfacial recognition site of this enzyme by the MALDI-TOF-MS peptide mapping analyses. (C) 1999 Elsevier Sci ence Ltd. All rights reserved.