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The Molecular Mechanism of Bee Venom Phospholipase A 2 Inactivation by Bolinaquinone
Author(s) -
Monti Maria Chiara,
Casapullo Agostino,
Santomauro Cosima,
D'Auria Maria Valeria,
Riccio Raffaele,
GomezPaloma Luigi
Publication year - 2006
Publication title -
chembiochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.05
H-Index - 126
eISSN - 1439-7633
pISSN - 1439-4227
DOI - 10.1002/cbic.200500454
Subject(s) - conjugate , chemistry , bee venom , non covalent interactions , covalent bond , molecular model , molecular mass , venom , natural product , combinatorial chemistry , stereochemistry , biochemistry , molecule , biology , organic chemistry , enzyme , mathematical analysis , zoology , hydrogen bond , mathematics
Abstract The molecular basis of the inactivation of bee venom PLA 2 by the marine natural product bolinaquinone (BLQ) was studied by several spectral techniques (CD, fluorescence, and NMR spectroscopy, mass spectrometry), biomimetic reactions, and molecular modeling. Our data suggest competitive inhibition based on a BLQ–PLA 2 noncovalent molecular recognition. However, BLQ is also able to react selectively with Lys133 through conjugate addition followed by a β elimination. The biological implications of both the covalent and noncovalent molecular events are discussed.