PMID: 11168405Feb 13, 2001

Prochiral selectivity in H(2)O(2)-promoted oxidation of arylalkanols catalysed by chloroperoxidase. The role of the interactions between the OH group and the amino-acid residues in the enzyme active site

European Journal of Biochemistry
E BaciocchiG Pochetti

Abstract

The H(2)O(2)-promoted oxidations of (R)-[alpha-(2)H(1)]-and (S)-[alpha-(2)H(1)]-arylalkanols catalysed by chloroperoxidase (CPO) from Caldariomyces fumago have been investigated. It has been found that with (R)-[alpha-(2)H(1)]-alcohols, the oxidation involves almost exclusively the cleavage of the C-H bond, whereas in the case of the oxidation of (S)-[alpha-(2)H(1)]-alcohols, the C-D bond is preferentially broken. These results clearly indicate that the reactions of corresponding undeuterated arylalkanols are characterized by a high prochiral selectivity, involving the cleavage of the pro-S C-H bond. This prochiral selectivity is poorly influenced by the electronic effect of ring substituents, whereas it decreases with the length of the carbon lateral chain, in the order: benzyl alcohol > 2-phenylethanol > 3-phenylpropanol. Molecular binding studies showed that the main factor directing the docking of the substrate in such a specific orientation in the enzyme active site is the interaction between the alcoholic OH group and the residue Glu183. This interaction is likely to drive both the stereochemistry and the regiochemistry of these reactions. A bifurcated hydrogen bond involving the OH group, the carboxylate oxygen of Glu183...Continue Reading

References

Apr 29, 1986·Biochemical and Biophysical Research Communications·J GeigertS L Neidleman
Aug 11, 1987·Biochemistry·S KobayashiA P Schaap
Feb 26, 1986·Biochemical and Biophysical Research Communications·S KobayashiA P Schaap
Aug 12, 1983·Biochemical and Biophysical Research Communications·J GeigertJ Wadsworth
Apr 1, 1981·Canadian Journal of Biochemistry·T AraisoH B Dunford
Jun 1, 1995·Archives of Biochemistry and Biophysics·V P MillerP R Ortiz de Montellano
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May 31, 1996·The Journal of Organic Chemistry·Frederick J. Lakner, Lowell P Hager

Citations

Aug 6, 2004·Applied and Environmental Microbiology·René UllrichMartin Hofrichter
Apr 22, 2006·Applied Microbiology and Biotechnology·Martin Hofrichter, René Ullrich
Mar 15, 2019·BMC Evolutionary Biology·Muniba FaizaYonghua Wang

Related Concepts

3-phenyl-1-propanol
4-(trifluoromethyl)benzyl alcohol
Anisyl alcohol
Anisoles
Benzyl Alcohols
Catalysis
Chloride Peroxidase
Yeast Proteins
Hydrogen Bonding
Oxydol

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