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Related Experiment Videos

Stereoinversions using microbial redox-reactions

A J Carnell1

  • 1Department of Chemistry, Robert Robinson Laboratories, University of Liverpool. acarnell@liverpool.ac.uk

Advances in Biochemical Engineering/Biotechnology
|February 6, 1999
PubMed
Summary
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This study reviews redox enzymes for stereoinversion of chiral alcohols, focusing on biocatalytic deracemization yielding valuable intermediates. Whole-cell systems efficiently achieve these reactions, offering high enantioselectivity and yield.

Area of Science:

  • Biocatalysis
  • Organic Chemistry
  • Enzyme Engineering

Background:

  • Chiral secondary alcohols are crucial synthetic intermediates.
  • Stereoselective synthesis remains a significant challenge in organic chemistry.
  • Biocatalysis offers a green and efficient alternative for chiral synthesis.

Purpose of the Study:

  • To summarize recent literature on redox enzyme-catalyzed stereoinversion of chiral secondary alcohols.
  • To highlight biotransformations achieving deracemization of racemic substrates to high-value intermediates.
  • To discuss the role of whole-cell systems and cofactor recycling in these reactions.

Main Methods:

  • Literature review of redox enzyme applications in stereoinversion.
  • Analysis of biotransformations using whole-cell systems.

Related Experiment Videos

  • Discussion of enantioselective and stereoselective deracemization strategies.
  • Exploration of enzymes like epimerases in biosynthesis.

    • Main Results:

    • Whole-cell biocatalysts enable efficient deracemization of racemic alcohols with high yields.
    • Enantioselective deracemization of mandelic acid and pantoyl lactone using enantiocomplementary microorganisms.
    • Stereoselective deracemization of various chiral alcohols (beta-hydroxyesters, aryl ethanols, diols) by single microorganisms.
    • Double stereoinversion demonstrated for substrates with multiple stereocenters.

    Conclusions:

    • Redox enzymes, particularly within whole-cell systems, are powerful tools for stereoinversion and deracemization.
    • Optimized reaction and growth conditions enhance selectivity in biocatalytic transformations.
    • Epimerases play a vital role in carbohydrate biosynthesis, with ongoing research into their mechanisms.