Naslov
Complex of Burkholderia cepacia lipase with transition state analogue of 1-phenoxy-2-acetoxybutane, Biocatalytic, structural and modelling study.

Autori
Luić, Marija ; Tomić, Sanja ; Leščić, Ivana ; Ljubović, Edina ; Šepac, Dragan ; Šunjić, Vitomir ; Vitale, Ljubinka ; Saenger, Wolfram ; Kojić-Prodić, Biserka

Izvornik
European Journal of Biochemistry (0014-2956) 268 (2001), 14; 3964-3973

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
Burkholderia cepacia lipase; Pseudomonas cepacia lipase; racemic sec alcohols; transition state (TS) analogue; crystal structure; molecular modelling

Sažetak
In a series of four racemic phenoxyalkyl-alkyl carbinols, 1-phenoxy-2-hydroxy butane (1) is enantioselectively acetylated by Burkholderia cepacia (formerly Pseudomonas cepacia) lipase with an E-value >200, whereas for the other three racemates E was found to be <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, (RP,SP)-methyl-O-(2R)-1-phenoxybut-2-yl) phosphonic acid chloride was prepared and crystallised 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.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

POVEZANOST RADA