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Received: 2005-04-28

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Journal of Zhejiang University SCIENCE B 2005 Vol.6 No.10 P.1028~1032

http://doi.org/10.1631/jzus.2005.B1028


Influence of kaolinite on chiral hydrolysis of methyl dichlorprop enantiomers


Author(s):  FANG Zhao-hua, WEN Yue-zhong, LIU Wei-ping

Affiliation(s):  Institute of Environmental Science, Zhejiang University, Hangzhou 310029, China

Corresponding email(s):   environment@zju.edu.cn

Key Words:  Enantioselectivity, Kaolinite, Chiral gas chromatography, Methyl dichlorprop, Lipase


FANG Zhao-hua, WEN Yue-zhong, LIU Wei-ping. Influence of kaolinite on chiral hydrolysis of methyl dichlorprop enantiomers[J]. Journal of Zhejiang University Science B, 2005, 6(10): 1028~1032.

@article{title="Influence of kaolinite on chiral hydrolysis of methyl dichlorprop enantiomers",
author="FANG Zhao-hua, WEN Yue-zhong, LIU Wei-ping",
journal="Journal of Zhejiang University Science B",
volume="6",
number="10",
pages="1028~1032",
year="2005",
publisher="Zhejiang University Press & Springer",
doi="10.1631/jzus.2005.B1028"
}

%0 Journal Article
%T Influence of kaolinite on chiral hydrolysis of methyl dichlorprop enantiomers
%A FANG Zhao-hua
%A WEN Yue-zhong
%A LIU Wei-ping
%J Journal of Zhejiang University SCIENCE B
%V 6
%N 10
%P 1028~1032
%@ 1673-1581
%D 2005
%I Zhejiang University Press & Springer
%DOI 10.1631/jzus.2005.B1028

TY - JOUR
T1 - Influence of kaolinite on chiral hydrolysis of methyl dichlorprop enantiomers
A1 - FANG Zhao-hua
A1 - WEN Yue-zhong
A1 - LIU Wei-ping
J0 - Journal of Zhejiang University Science B
VL - 6
IS - 10
SP - 1028
EP - 1032
%@ 1673-1581
Y1 - 2005
PB - Zhejiang University Press & Springer
ER -
DOI - 10.1631/jzus.2005.B1028


Abstract: 
The effect of kaolinite on the enzymatic chiral hydrolysis of methyl dichlorprop enantiomers ((R,S)-methyl-2-(2,4-dichlorophenoxy) propanoic acid, 2,4-DPM) was investigated using chiral gas chromatography. Compared with the control without kaolinite, the enantiomeric ratio (ER) increased from 1.35 to 8.33 and the residual ratio of 2,4-DPM decreased from 60.89% to 41.55% in the presence of kaolinite. kaolinite likely had emotion influence on lipase activity and its enantioselectivity. Moreover, the amount of kaolinite added was also found to be a sensitive factor affecting the enantioselective hydrolysis of 2,4-DPM. Fourier transform infrared (FTIR) spectroscopy studies of the interaction of lipase with kaolinite provided insight into the molecular structure of the complex and offered explanation of the effects of kaolinite on enzymatic hydrolysis of 2,4-DPM. Spectra showed that the effect of kaolinite on the hydrolysis of 2,4-DPM was affected by adsorption of lipase on kaolinite and changes of adsorbed lipase conformation, which led to the modified enantioselectivity.

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Reference

[1] de Fuentes, I.E., Viseras, C.A., Ubiali, D., Terreni, M., Alcantara, A.R., 2001. Different phyllosilicates as supports for lipase immobilization. Journal of Molecular Catalysis B: Enzymatic, 11(4-6):657-663.

[2] Fernandez-Lorente, G., Terreni, M., Mateo, C., Bastida, A., Fernandez-Lafuente, R., Dalmases, P., Huguet, J., Guisan, J.M., 2001. Modulation of lipase properties in macro-aqueous systems by controlled enzyme immobilization: enantioselective hydrolysis of a chiral ester by immobilized Pseudomonas lipase. Enzyme and Microbial Technology, 28:389-396.

[3] Huang, P.M., Senesi, N., Buffle, J., 1998. Structure and Surface Reactions of Soil Particles. Wiley, New York, p.449-479.

[4] Jaeger, K.E., Ransac, S., Dijkstra, B.W., Colson, C., van Heuvel, M., Misset, O., 1994. Bacterial lipases. FEMS Microbiology Reviews, 15:29-63.

[5] Marten, E., Muller, R.J., Deckwer, W.D., 2003. Studies on the enzymatic hydrolysis of polyesters: I. Low molecular mass model esters and aliphatic polyesters. Polymer Degradation and Stability, 80:485-501.

[6] Monroy-Noyola, A., Sogorb, M.A., Vilanova, E., 1999. Enzyme concentration as an important factor in the in vitro testing of the stereospecificity of the enzymatic hydrolysis of organophosphorus compounds. Toxicology in Vitro, 13:689-692.

[7] Palomo, J.M., Fernandez-Lorente, G., Mateo, C., Ortiz, C., Fernandez-Lafuente, R., Guisan, J.M., 2002. Modulation of the enantioselectivity of lipases via controlled immobilization and medium engineering: hydrolytic resolution of mandelic acid esters. Enzyme and Microbial Technology, 31:775-783.

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