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@article{360452,
author = {Trantírek, Lukáš and Hynková, Kamila and Nagata, Yuji and Murzin, Alexey and Ansorgová, Alena and Sklenář, Vladimír and Damborský, Jiří},
article_number = {11},
language = {eng},
journal = {Journal of Biological Chemistry},
title = {Reaction mechanism and stereochemistry of gamma-hexachlorocyclohexane dehydrochlorinase LinA},
url = {http://www.ncbr.chemi.muni.cz/~jiri/ABSTRACTS/jbc01.html},
volume = {276},
year = {2001}
}
TY - JOUR
ID - 360452
AU - Trantírek, Lukáš - Hynková, Kamila - Nagata, Yuji - Murzin, Alexey - Ansorgová, Alena - Sklenář, Vladimír - Damborský, Jiří
PY - 2001
TI - Reaction mechanism and stereochemistry of gamma-hexachlorocyclohexane dehydrochlorinase LinA
JF - Journal of Biological Chemistry
VL - 276
IS - 11
SP - 7734
EP - 7734
UR - http://www.ncbr.chemi.muni.cz/~jiri/ABSTRACTS/jbc01.html
N2 - 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.
ER -
TRANTÍREK, Lukáš, Kamila HYNKOVÁ, Yuji NAGATA, Alexey MURZIN, Alena ANSORGOVÁ, Vladimír SKLENÁŘ a Jiří DAMBORSKÝ. Reaction mechanism and stereochemistry of gamma-hexachlorocyclohexane dehydrochlorinase LinA. \textit{Journal of Biological Chemistry}. 2001, roč.~276, č.~11, s.~7734-7740.
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