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


Luić, Marija; Tomić, Sanja; Leščić, Ivana; Ljubović, Edina; Šepac, Dragan; Šunjić, Vitomir; Vitale, Ljubinka; Saenger, Wolfram; Kojić-Prodić, Biserka
Complex of Burkholderia cepacia lipase with transition state analogue of 1-phenoxy-2-acetoxybutane, Biocatalytic, structural and modelling study. // European Journal of Biochemistry, 268 (2001), 14; 3964-3973 (međunarodna recenzija, članak, znanstveni)


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

Časopis indeksira:


  • Current Contents Connect (CCC)
  • Web of Science Core Collection (WoSCC)
    • Science Citation Index Expanded (SCI-EXP)
    • SCI-EXP, SSCI i/ili A&HCI
  • Scopus
  • MEDLINE