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An Overview on the Enhancement of Enantioselectivity and Stability of Microbial Epoxide Hydrolases

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Abstract

Epoxide hydrolases (EHs; 3.3.2.x) catalyze the enantioselective ring opening of racemic epoxides to the corresponding enantiopure vicinal diols and remaining equivalent unreacted epoxides. These epoxides and diols are used for the synthesis of chiral drug intermediates. With an upsurge in the methods for identification of novel microbial EHs, a lot of EHs have been discovered and utilized for kinetic resolution of racemic epoxides. However, there is still a constraint on the account of limited EHs being successfully applied on the preparative scale for industrial biotransformations. This limitation has to be overcome before application of identified functional EHs on large scale. Many strategies such as optimizing reaction media, immobilizing EHs and laboratory-scale directed evolution of EHs have been adopted for enhancing the industrial potential of EHs. In this review, these approaches have been highlighted which can serve as a pathway for the enrichment of already identified EHs for their application on an industrial scale in future studies.

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Abbreviations

EHs:

Epoxide hydrolase

ILs:

Ionic liquids

DESs :

Deep eutectic solvents

DMSO:

Dimethylsulfoxide

HBDs:

Hydrogen bond donors

EDA:

Ethylenediamine

IDA:

Iminodiacetic acid

CPG:

Calcium pectate gelled

SA:

Sodium alginate

CS:

Cellulose sulfate

PMCG:

Poly (methylene-co-guanidine)

Fmoc-FF:

Fluorenylmethoxycarbonyl diphenylalanine

PEI:

Polymer, polyethyleneimine

CLEAS:

Cross-linked enzyme aggregates

epPCR:

Error-prone polymerase chain reaction

PCR:

Polymerase chain reaction

ISM:

Iterative saturation mutagenesis

CAST:

Combinatorial Active Site Saturation Test

B-FIT:

B-Factor Iterative Test

ASRA:

Adaptive substituent reordering algorithm

FRESCO:

Framework for Rapid Enzyme Stabilization by Computational Libraries

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Acknowledgements

This work was financially supported by Department of Biotechnology (DBT) via Grant No. BT/PR/4694/PID/6/633/2012, Government of India, New Delhi. PS gratefully acknowledge DBT for the SRF. The financial assistance received from Department of Science and Technology-Promotion of University Research and Scientific Excellence (DST-PURSE) and University Grants Commission-Special Assistance Programme (UGC-SAP) (DRS Phase-I) is duly acknowledged.

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  1. Department of Biochemistry, Panjab University, Sector 25, BMS Block II, Chandigarh, 160014, India

    Priya Saini & Dipti Sareen

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Saini, P., Sareen, D. An Overview on the Enhancement of Enantioselectivity and Stability of Microbial Epoxide Hydrolases. Mol Biotechnol 59, 98–116 (2017). https://doi.org/10.1007/s12033-017-9996-8

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