Evaluation of chiral α-cyanoesters as general fluorescent substrates for screening enantioselective esterases

Huazhang Huang, Kosuke Nishi, Shirley J. Gee, Bruce D. Hammock

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

Esterases play a crucial role in industrial chemical synthesis, maintaining normal physiological metabolism and detoxifying exogenous ester-containing toxicants. To meet the rapidly increasing industrial need for all kinds of esterases, especially enantioselective esterases used to generate highly pure chiral compounds, general substrates are necessary for rapid screening, monitoring, purification, and characterization. In this study, general fluorescent substrates including phenolic derivatives and α-cyanoesters were evaluated for sensitivity in detecting esterases in buffer systems. Results with two different esterases and different incubation times suggested that the α-cyanoesters examined were significantly more sensitive at detecting esterases than the corresponding tested phenolic derivatives. More importantly, α-cyanoesters, containing a secondary alcohol, possess at least one chiral center; thus, they are tools to screen for enantioselective hydrolysis. Results indicated that the enantioselectivity of esterases toward general α-cyanoesters strongly depended on the esterase and the substrate, but the majority of esterases examined preferred S-isomers to their corresponding R-enantiomers. Most appealing was the very high enantioselectivity displayed in cytosolic esterases of the house fly. The potential utility of such esterases is discussed. In addition, the use of α-cyanoesters as chiral fluorescent substrates was demonstrated for monitoring in enantioselective esterases.

Original languageEnglish (US)
Pages (from-to)694-699
Number of pages6
JournalJournal of Agricultural and Food Chemistry
Volume54
Issue number3
DOIs
StatePublished - Feb 8 2006

Fingerprint

Esterases
esterases
Screening
screening
Substrates
enantiomers
Enantioselectivity
chemical derivatives
Derivatives
Industrial chemicals
Enantiomers
Monitoring
monitoring
Musca domestica
toxic substances
Metabolism
Diptera
Isomers
Purification
isomers

Keywords

  • Chiral fluorescent substrates
  • Enantioselectivity
  • Esterases
  • Partial purification

ASJC Scopus subject areas

  • Agricultural and Biological Sciences (miscellaneous)
  • Food Science
  • Chemistry (miscellaneous)

Cite this

Evaluation of chiral α-cyanoesters as general fluorescent substrates for screening enantioselective esterases. / Huang, Huazhang; Nishi, Kosuke; Gee, Shirley J.; Hammock, Bruce D.

In: Journal of Agricultural and Food Chemistry, Vol. 54, No. 3, 08.02.2006, p. 694-699.

Research output: Contribution to journalArticle

Huang, Huazhang ; Nishi, Kosuke ; Gee, Shirley J. ; Hammock, Bruce D. / Evaluation of chiral α-cyanoesters as general fluorescent substrates for screening enantioselective esterases. In: Journal of Agricultural and Food Chemistry. 2006 ; Vol. 54, No. 3. pp. 694-699.
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