1HQD

PSEUDOMONAS CEPACIA LIPASE COMPLEXED WITH TRANSITION STATE ANALOGUE OF 1-PHENOXY-2-ACETOXY BUTANE

Summary for 1HQD

• Entry DOI: 10.2210/pdb1hqd/pdb
• Related: 1OIL 2LIP 3LIP 4LIP 5LIP
• Descriptor: LIPASE, CALCIUM ION, (RP,SP)-O-(2R)-(1-PHENOXYBUT-2-YL)-METHYLPHOSPHONIC ACID CHLORIDE, ... (4 entities in total)
• Functional Keywords: pseudomonas cepacia lipase, racemic sec alcohols, transition state (ts) analogue, molecular modelling, hydrolase
• Biological source: Burkholderia cepacia
• Total number of polymer chains: 1
• Total formula weight: 33453.51

Authors

Luic, M.,Tomic, S.,Lescic, I.,Ljubovic, E.,Sepac, D.,Sunjic, V.,Vitale, L.,Saenger, W.,Kojic-Prodic, B. (deposition date: 2000-12-15, release date: 2001-08-22, Last modification date: 2024-11-20)

Primary citation

Luic, M.,Tomic, S.,Lescic, I.,Ljubovic, E.,Sepac, D.,Sunjic, V.,Vitale, L.,Saenger, W.,Kojic-Prodic, B.
Complex of Burkholderia cepacia lipase with transition state analogue of 1-phenoxy-2-acetoxybutane: biocatalytic, structural and modelling study.
Eur.J.Biochem., 268:3964-3973, 2001

PubMed 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.

PubMed: 11453990
DOI: 10.1046/j.1432-1327.2001.02303.x

Experimental method

X-RAY DIFFRACTION (2.3 Å)