Chiral epoxide production using mycobacterium solubilized in a water-in-oil microemulsion

S. Prichanont, D. J. Leak, D. C. Stuckey

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

The application of many biotransformation processes is limited because the substrates/products are poorly water soluble, can be further metabolized, or are inhibitory. Hence non-aqueous media (e.g. two-phase systems, low water environments) are being examined to determine whether they can be used to overcome these problems. One novel approach is to encapsulate whole cells in water-in-oil (w/o) microemulsions (reverse micelles). In this study we have investigated the influence of key system parameters on system stability and epoxidation activity of Mycobacterium M156 cells in reverse micelles comprised of a mixture of Tween 85 and Span 80 (10-20 w%, with an hydrophilic/lipophilic balance [HLB] of 10 and a weight ratio of Tween 85 to Span 80 = 5.7) in n-hexadecane. It was found that the minimum allyl phenyl ether (APE) concentration required in the bulk hexadecane solvent phase for epoxidation to occur was 15 mM, whereas the minimum molar ratio of water to surfactant (W0) was 35. The optimum epoxidation rate achieved was 3.8 nmol/mg dwt-min with an APE concentration of 50 mM, and a W0 of 50, with an enantiomeric excess (ee) of 86%. However, epoxidation was found to terminate approximately 3 h after initiation, and the causes for this were postulated to be either: the deleterious effect of the solvent on the Mycobacteria; inactivation of the energy generating system; an insufficient energy supply, or; the instability of the monooxygenase enzyme. It was concluded that on balance emulsion systems are not an economically viable system for producing phenyl glycidyl ether (PGE). Copyright (C) 2000 Elsevier Science Inc.

Original languageEnglish
Pages (from-to)134-142
Number of pages9
JournalEnzyme and Microbial Technology
Volume27
Issue number1-2
Early online date20 Jun 2000
DOIs
Publication statusPublished - 1 Jul 2000

Fingerprint

Epoxidation
Epoxy Compounds
Microemulsions
Mycobacterium
Polysorbates
Oils
Ethers
Water
Micelles
Biotransformation
Mixed Function Oxygenases
Emulsions
System stability
Surface-Active Agents
Surface active agents
Enzymes
Weights and Measures
Substrates
phenyl allyl ether
n-hexadecane

Keywords

  • Biotransformation
  • Cell encapsulation
  • Chiral epoxide
  • Reverse micelles

ASJC Scopus subject areas

  • Biochemistry
  • Biotechnology
  • Applied Microbiology and Biotechnology

Cite this

Chiral epoxide production using mycobacterium solubilized in a water-in-oil microemulsion. / Prichanont, S.; Leak, D. J.; Stuckey, D. C.

In: Enzyme and Microbial Technology, Vol. 27, No. 1-2, 01.07.2000, p. 134-142.

Research output: Contribution to journalArticle

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