Hydrolytic kinetic resolution of the enantiomers of the structural isomers trans-1-phenylpropene oxide and (2,3-epoxypropyl)benzene by yeast epoxide hydrolase

@article{Lotter2004HydrolyticKR,
  title={Hydrolytic kinetic resolution of the enantiomers of the structural isomers trans-1-phenylpropene oxide and (2,3-epoxypropyl)benzene by yeast epoxide hydrolase},
  author={Jeanette Lotter and Adriana Leonora Botes and Martha S. van Dyk and Jaco C. Breytenbach},
  journal={Biotechnology Letters},
  year={2004},
  volume={26},
  pages={1197-1200}
}
Kinetic resolution of the enantiomers of trans-1-phenylpropene oxide and (2,3-epoxypropyl)benzene was achieved by yeasts from the genus Rhodotorula. The resolution of trans-1-phenylpropene oxide by Rhodotorula glutinis UOFS Y-0123 yielded (1R,2R)-epoxide (ee >98%, yield 30%) and (1R,2S)-diol (ee 95%, yield 40%). The highest enantio- and regioselectivity toward (2,3-epoxypropyl)benzene resided in Rhodotorula sp. UOFS Y-0448 (E = 6.16), yielding (S)-epoxide (ee 64%, yield 33%) and (R)-diol (ee 67… 

Modification of Substrate Specificity Resulting in an Epoxide Hydrolase with Shifted Enantiopreference for (2,3‐Epoxypropyl)benzene

Random mutagenesis targeted at hotspots of noncatalytic active‐site residues of potato epoxide hydrolase StEH1 combined with an enzyme‐activity screen allowed the isolation of enzyme variants

Further Characterization of Recombinant Epoxide Hydrolase Kau2 Derived from Metagenomic DNA and Application in Biocatalytic Reactions

The PhD work described in this dissertation was conducted in order to get insights about a newly discovered epoxide hydrolase (EH) from a metagenomic analysis of a biofilter.

Cloning of an epoxide hydrolase‐encoding gene from Rhodotorula mucilaginosa and functional expression in Yarrowia lipolytica

Whole‐cell biotransformation of (2,3‐epoxypropyl)benzene, using the recombinant EH, revealed activity and selectivity far superior to any other activity andSelectivity reported in literature using wild‐type organisms.

Epoxide hydrolase and its application in organic synthesis

Recent progress in molecular biology and enzyme-related research areas enabled and simplified the production and purification of recombinant enzymes in large quantities and their engineering towards tailor-made biocatalysts using straightforward mutagenesis and screening techniques.

Temperature and pH dependence of enzyme-catalyzed hydrolysis of trans-methylstyrene oxide. A unifying kinetic model for observed hysteresis, cooperativity, and regioselectivity.

It is proposed that hysteresis, regioselectivity, and, when applicable, hysteretic cooperativity are closely linked properties, explained by the kinetic mechanism earlier introduced by this group.

References

SHOWING 1-10 OF 21 REFERENCES

Enantioselectivities of yeast epoxide hydrolases for 1,2-epoxides

High-yield Production of Optically Active 1,2-Diols from the Corresponding Racemates by Microbial Stereoinversion

A novel method for producing optically active 1,2-diols by microbial Stereoinversion was developed. It was found that some microorganisms could convert only (R)-1,2-pentanediol in the racemate to the

Stereoselectivities of microbial epoxide hydrolases.

A simple method to determine the enantiomeric ratio in enantioselective biocatalysis.

Biocatalytic conversion of epoxides.