Substrate specificity of lipases in alkoxycarbonylation reaction: QSAR model development and experimental validation

Biotechnology and Bioengineering
Sangeetha M ChandrasekaranPramod P Wangikar

Abstract

Although lipases are known to catalyze alkoxycarbonylation reactions in organic solvents, the existing knowledge base on their substrate specificity in alkoxycarbonylation reaction is sparse. Moreover, models to predict substrate specificity have not been reported. Here, we report the experimentally measured rate constants for 180 acyl donor-alcohol pairs and demonstrate the two-step synthesis of over 70 disubstituted carbonate products from simple precursors such as diphenyl carbonate and alcohols. The efficiency of synthesis was found to be dependent on the order of alcohol addition. This motivated the need to develop a model to predict lipase specificity in alkoxycarbonylation reactions. A partial least square model has been developed to correlate the reaction rate with (i) descriptors of alcohol for a fixed acyl donor, (ii) descriptors of acyl donor for a fixed alcohol, (iii) descriptors of both the acyl donor and the alcohol. The number of descriptors being far greater than the number of observations was a potential limitation in the model development. This was addressed by selecting a subset of descriptors using a systematic procedure based on (a) correlation among the descriptors and step-wise regression methodology, and...Continue Reading

References

Sep 26, 1995·Biochemistry·P P WangikarJ S Dordick
Mar 6, 1999·Current Opinion in Microbiology·J S DordickM V Sergeeva
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Feb 13, 2003·Journal of Molecular Biology·Pramod P WangikarSunita Sarawagi
Mar 26, 2003·Journal of Computer-aided Molecular Design·Lennart ErikssonSvante Wold
Apr 5, 2003·Biotechnology Progress·Sangeetha M Chandrasekaran, Pramod P Wangikar
Jun 12, 2003·Biotechnology and Bioengineering·S V Suresh KumarPramod P Wangikar
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May 5, 1996·Biotechnology and Bioengineering·P P WangikarJ S Dordick
Sep 1, 2004·Environmental Toxicology and Pharmacology·Junfeng Niu, Gang Yu

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