Detailed Information on Publication Record
2001
Reaction mechanism and stereochemistry of gamma-hexachlorocyclohexane dehydrochlorinase LinA
TRANTÍREK, Lukáš, Kamila HYNKOVÁ, Yuji NAGATA, Alexey MURZIN, Alena ANSORGOVÁ et. al.Basic information
Original name
Reaction mechanism and stereochemistry of gamma-hexachlorocyclohexane dehydrochlorinase LinA
Authors
TRANTÍREK, Lukáš (203 Czech Republic), Kamila HYNKOVÁ, Yuji NAGATA, Alexey MURZIN, Alena ANSORGOVÁ (203 Czech Republic), Vladimír SKLENÁŘ (203 Czech Republic) and Jiří DAMBORSKÝ (203 Czech Republic)
Edition
Journal of Biological Chemistry, 2001
Other information
Language
English
Type of outcome
Článek v odborném periodiku
Field of Study
10600 1.6 Biological sciences
Country of publisher
United States of America
Confidentiality degree
není předmětem státního či obchodního tajemství
References:
RIV identification code
RIV/00216224:14310/01:00004145
Organization unit
Faculty of Science
UT WoS
000167474900011
Změněno: 28/5/2003 22:04, prof. Mgr. Jiří Damborský, Dr.
Abstract
V originále
g-hexachlorocyclohexane dehydrochlorinase (LinA) catalyses the initial steps in the biotransformation of the important insecticide g-hexachlorocyclohexane (g-HCH) by the soil bacterium Sphingomonas paucimobilis UT26. Stereochemical analysis of the reaction products formed during conversion of g-HCH by LinA was investigated by GC-MS, NMR, CD and molecular modeling. The NMR spectra of 1,3,4,5,6-pentachlorocyclohexene (PCCH) produced from g-HCH using either enzymatic dehydrochlorination or alkaline dehydrochlorination were compared and found to be identical. Both enantiomers present in the racemate of synthetic g-PCCH were converted by LinA, each at a different rate. 1,2,4-trichlorobenzene (1,2,4-TCB) was detected as the only product of the biotransformation of biosynthetic g-PCCH. 1,2,4-TCB and 1,2,3-TCB were identified as the dehydrochlorination products of racemic g-PCCH. d-PCCH was detected as the only product of dehydrochlorination of d-HCH. LinA requires the presence of a 1,2-biaxial HCl pair on a substrate molecule. LinA enantiotopologically differentiates two 1,2-biaxial HCl pairs present on g-HCH and gives rise to a single PCCH enantiomer 1,3(R),4(S),5(S),6(R)-PCCH. Furthermore, LinA enantiomerically differentiates 1,3(S),4(R),5(R),6(S)-PCCH and 1,3(R),4(S),5(S),6(R)-PCCH. The proposed mechanism of enzymatic biotransformation of g-HCH to 1,2,4-TCB by LinA consists of two 1,2-anti conformationally dependent dehydrochlorinations followed by 1,4-anti dehydrochlorination.
Links
GA203/97/P149, research and development project |
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LN00A016, research and development project |
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ME 276, research and development project |
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