title: Complex of Burkholderia cepacia lipase with transition state analogue of 1-phenoxy-2-acetoxybutane: biocatalytic, structural and modelling study.
abstract: In a series of four racemic phenoxyalkyl-alkyl carbinols, 1-phenoxy-2-hydroxybutane (1) is enantioselectively acetylated by Burkholderia cepacia (formerly Pseudomonas cepacia) lipase with an E value > or = 200, whereas for the other three racemates E was found to be < or = 4. To explain the high preference of B. cepacia lipase for (R)-(+)-1, a precursor of its transition state analogue with a tetrahedral P-atom, (R(P),S(P))-O-(2R)-(1-phenoxybut-2-yl)methylphosphonic acid chloride was prepared and crystallized in complex with B. cepacia lipase. The X-ray structure of the complex was determined, allowing to compare the conformation of the inhibitor with results of molecular modelling.
authors.affiliation: Rudjer Boskovic Institute, Zagreb, Croatia] Institut für Chemie-Kristallographie, Freie Universität Berlin, Germany. luic@faust.irb.hr
authors.forename: M
authors.initials: M
authors.lastname: Luić
authors.forename: S
authors.initials: S
authors.lastname: Tomić
authors.forename: I
authors.initials: I
authors.lastname: Lescić
authors.forename: E
authors.initials: E
authors.lastname: Ljubović
authors.forename: D
authors.initials: D
authors.lastname: Sepac
authors.forename: V
authors.initials: V
authors.lastname: Sunjić
authors.forename: L
authors.initials: L
authors.lastname: Vitale
authors.forename: W
authors.initials: W
authors.lastname: Saenger
authors.forename: B
authors.initials: B
authors.lastname: Kojic-Prodić
mesh_terms: D016956:Burkholderia cepacia / Q000201:enzymology*; D002384:Catalysis; D018360:Crystallography, X-Ray; D006860:Hydrogen Bonding; D008049:Lipase / Q000037:antagonists & inhibitors / Q000737:chemistry* / Q000378:metabolism; D008958:Models, Molecular; D009943:Organophosphorus Compounds / Q000378:metabolism*; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: C432663:O-(1-phenoxybut-2-yl)methyl phosphonic acid chloride; D009943:Organophosphorus Compounds; D008049:Lipase