• Open Access

Chiral transformations by microbial enzymes

An annotated selection of World Wide Web sites relevant to the topics in Microbial Biotechnology

Authors

  • Lawrence P. Wackett

    1. McKnight Professor and Head
      Microbial Biochemistry and Biotechnology
      Department of Biochemistry
      Molecular Biology and Biophysics
      University of Minnesota
      St Paul, MN 55108, USA
    Search for more papers by this author

Microbial hydantoinases to make D-amino acids

http://tejas.serc.iisc.ernet.in/currsci/jul10/articles20.htm

This web paper describes the utility and production of D-amino acids using microbial hydantoinases. An extensive set of references are provided.

Microbial Baeyer-Villiger oxygenases

http://chimlum-186.univ-mrs.fr/Mes-sites-WEB-Anglais/bayer_villigerases.htm

This web page shows numerous target compounds, largely pharmaceuticals, which can be made via synthetic steps involving microbial Baeyer-Villiger monooxygenases.

Biodegradation of chiral pollutants

http://www.epa.gov/nerl/research/1999/html/g8-4.html

A significant number of pesticides are chiral. Different enantiomers can show marked differences in their biodegradation rates, as discussed on this web page.

Microbial biotransformations for drug precursors

http://www.bioline.org.br/request?au01026

This web report addresses microbial chiral transformations for generating synthetic intermediates for pharmaceutical compounds. There is a particular emphasis on fungal transformation of steroid compounds.

Microbial enantioselective sulfatases

http://www.aseanbiotechnology.info/Abstract/21022648.pdf

This article describes the use of microbial sulfatases for enantio-convergent transformations to generate single enantiomer products in high yield.

Chiral synthesis

http://www.iccas.ac.cn/english/html/2004-8-20/2004820143856.htm

This web page focuses on chiral synthesis with some examples of microbial enzymatic chiral resolutions.

Enantioselective microbial epoxide hydrolases

http://www.biocatalyse.univ-mrs.fr/Mes-sites-WEB-Anglais/epoxyde_hydrolases.htm

This web page shows numerous target compounds, largely pharmaceuticals, which can be made via synthetic steps involving microbial epoxide hydrolases.

Biotransformation of non-natural compounds

http://borgc185.kfunigraz.ac.at/Sites/Biocat.htm

This web page provides an excellent overview of enzymes in biocatalysis. Most of the enzymes derive from microbes and many of the transformations are desired because they produce chiral products.

Patent for microbial chiral sulfoxidation and amidation reactions

http://www.wipo.int/pctdb/en/wo.jsp?IA=WO2007027328&wo=2007027328&DISPLAY=DESC

This patent describes a microbial transformation process embodying a green chemical route to the pharmaceutical compound modafinil.

Biocatalysis and chiral resolution

http://pubs.acs.org/cen/coverstory/84/8433chiralchem3.html

This article in Chemical and Engineering News provides an excellent industrial perspective on the use of enzymes in chiral synthesis.

Cambrex: Chiral amines via transaminases

http://www.cambrex.com/Content/pharma/article.asp?ClassId=106&ContentId=479

Prochiral ketones can be converted to chiral amines. (R)- and (S)-specific microbial aminotransferases can be used to make whichever enantiomer is desired for a specific application.

Lipase database

http://www.au-kbc.org/beta/bioproj2/index.html

Lipases are perhaps the most widely used industrial enzymes in chiral resolutions. Lipases from the yeast Candida have been widely used, but bacterial enzymes have also proven useful.

Lipase engineering database

http://www.led.uni-stuttgart.de/

This web database deals with the α/β hydrolase fold enzymes, that include lipases and epoxide hydrolases.

Terpene cyclases structure/function

http://sfld.rbvi.ucsf.edu/cgi-bin/SFLDvm.py?view=superfamily&id=5

Terpene cyclases, or terpene synthases, control terpene carbon unit condensations, ultimately determining the stereochemistry of the products. This page in the Structure Function Linkage Database contains extensive information on this protein family.

Toluene dioxygenase reactions

http://umbbd.msi.umn.edu/tol/tdo.html

Toluene dioxygenase is a broad-specificity enzyme that produces chiral diols and alcohols, some of which have been used as chiral synthons. This page contains a table with the 109 known reactions, with links to further information.

Manufacturing chemist: Enzymes to the rescue

http://www.manufacturing-chemist.info/story.asp?storycode=40034

This page reviews some of the enzymatic chiral transformations that have proven to be most important industrially.

Dow: Industrial enzymes

http://pharma.dow.com/pharma/sm_molecules/capabilities/enzymeclass.htm

On this page, the Dow Chemical Company highlights their collection of industrial enzymes and microorganisms.

Ancillary