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An investigation of enzymatic kinetic resolution of racemic clopidogrel

Gaber, Yasser ; Amin Magdy, A and Hatti-Kaul, Rajni LU (2014) In Asian Journal of Microbiology, Biotechnology and Environmental Sciences 16(2). p.247-251
Abstract
This paper presents a biocatalysis based approach for asymmetric hydrolysis of Clopidogrel, one of the most effective antiplatelet aggregators. Instead of the conventional "wet lab" screening method, we used an advanced chemical information retrieval tool, Scifinder®, to find suitable enzyme candidate(s) for the asymmetric hydrolysis. Scifinder® search for reactions similar to the target reaction retrieved three potential hits: horse liver esterase, chymotrypsin and Candida rugosa lipase. Among the three, horse liver esterase was experimentally found to hydrolyse the correct isomer (R) of the racemic clopidogrel. Investigation of the effect of different water miscible co-solvents showed DMSO to provide the highest enantiomeric excess (ee)... (More)
This paper presents a biocatalysis based approach for asymmetric hydrolysis of Clopidogrel, one of the most effective antiplatelet aggregators. Instead of the conventional "wet lab" screening method, we used an advanced chemical information retrieval tool, Scifinder®, to find suitable enzyme candidate(s) for the asymmetric hydrolysis. Scifinder® search for reactions similar to the target reaction retrieved three potential hits: horse liver esterase, chymotrypsin and Candida rugosa lipase. Among the three, horse liver esterase was experimentally found to hydrolyse the correct isomer (R) of the racemic clopidogrel. Investigation of the effect of different water miscible co-solvents showed DMSO to provide the highest enantiomeric excess (ee) value of 20% at 43% conversion of the racemic ester, while a dicyanamide based ionic liquid as a co-solvent showed 12% ee. This article demonstrates the potential of the chemical databases as a possible rapid, resource-efficient tool to find an appropriate selective biocatalyst. (Less)
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author
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organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Asian Journal of Microbiology, Biotechnology and Environmental Sciences
volume
16
issue
2
pages
247 - 251
external identifiers
  • scopus:84907308934
language
English
LU publication?
yes
id
5a6ee405-3e7b-49ef-9d5e-a0314d89f125
date added to LUP
2019-06-28 01:04:03
date last changed
2021-08-11 04:26:39
@article{5a6ee405-3e7b-49ef-9d5e-a0314d89f125,
  abstract     = {This paper presents a biocatalysis based approach for asymmetric hydrolysis of Clopidogrel, one of the most effective antiplatelet aggregators. Instead of the conventional "wet lab" screening method, we used an advanced chemical information retrieval tool, Scifinder®, to find suitable enzyme candidate(s) for the asymmetric hydrolysis. Scifinder® search for reactions similar to the target reaction retrieved three potential hits: horse liver esterase, chymotrypsin and Candida rugosa lipase. Among the three, horse liver esterase was experimentally found to hydrolyse the correct isomer (R) of the racemic clopidogrel. Investigation of the effect of different water miscible co-solvents showed DMSO to provide the highest enantiomeric excess (ee) value of 20% at 43% conversion of the racemic ester, while a dicyanamide based ionic liquid as a co-solvent showed 12% ee. This article demonstrates the potential of the chemical databases as a possible rapid, resource-efficient tool to find an appropriate selective biocatalyst.},
  author       = {Gaber, Yasser and Amin Magdy, A and Hatti-Kaul, Rajni},
  language     = {eng},
  number       = {2},
  pages        = {247--251},
  series       = {Asian Journal of Microbiology, Biotechnology and Environmental Sciences},
  title        = {An investigation of enzymatic kinetic resolution of racemic clopidogrel},
  volume       = {16},
  year         = {2014},
}