title: The absolute configuration of belactin A, a beta-lactone-containing serine carboxypeptidase inhibitor: importance of the beta-lactone structure for serine carboxypeptidase inhibition.
abstract: The absolute configuration of belactin A, a beta-lactone-containing serine carboxypeptidase inhibitor was studied by a crystal X-ray diffraction analysis and its absolute structure was determined to be (2R,3S)-2-¿(3S)-3-[(2-amino-5-chlorophenyl)carboxamido]-1,1-dimethyl-2-o xobutyl¿-3-methyl-4-oxooxetane. The importance of the beta-lactone structure for inhibitory activity was found by preparing several derivatives of belactin A.
authors.affiliation: Institute of Microbial Chemistry, Tokyo, Japan.
authors.forename: S
authors.initials: S
authors.lastname: Murakami
authors.forename: Y
authors.initials: Y
authors.lastname: Takahashi
authors.forename: T
authors.initials: T
authors.lastname: Takeuchi
authors.forename: Y
authors.initials: Y
authors.lastname: Kodama
authors.forename: T
authors.initials: T
authors.lastname: Aoyagi
mesh_terms: D001549:Benzamides / Q000737:chemistry*; D002268:Carboxypeptidases / Q000037:antagonists & inhibitors* / Q000737:chemistry / Q000378:metabolism; D043402:Cathepsin A; D003460:Crystallization; D004791:Enzyme Inhibitors / Q000737:chemistry; D020128:Inhibitory Concentration 50; D007783:Lactones / Q000737:chemistry*; D014961:X-Ray Diffraction
chemical_list: D001549:Benzamides; D004791:Enzyme Inhibitors; D007783:Lactones; C098701:belactin A; D002268:Carboxypeptidases; D043402:Cathepsin A; C022633:serine carboxypeptidase