Jump to main content
Jump to site search

Issue 6, 2008
Previous Article Next Article

Stereoselective oxidation of R-(+)-limonene by chloroperoxidase from Caldariomyces fumago

Author affiliations

Abstract

The oxidation of R-(+)-limonene by chloroperoxidase (CPO) from Caldariomyces fumago is reported. The reaction was performed in 60 mM phosphate buffer at pH 3.0 and 6.0, and in the absence and in the presence of chloride ions. In the absence of chloride ions, at both pH values, the reaction was regio and stereoselective with a diasteromeric excess (de) >99% of (1S,2S)-4R-limonene-1,2-diol. On the other hand, when the reaction was carried out in the presence of chloride ions an enhancement in the reaction rate was observed, maintaining the regioselectivity, but not the stereoselectivity (de <5.4). The reaction products under these conditions were identified as (1S,2S)-4R-limonene-1,2-diol and (1R,2R)-4R-limonene-1,2-diol. It seems that in the absence of chloride ions the stereoselectivity is determined by stereospecific interaction of limonene with CPO active site, as supported by docking analysis, while in the presence of potassium chloride the limonene oxidation also occurs by the produced hypochlorite without stereoselectivity.

Graphical abstract: Stereoselective oxidation of R-(+)-limonene by chloroperoxidase from Caldariomyces fumago

Back to tab navigation

Publication details

The article was received on 02 Jan 2008, accepted on 02 Apr 2008 and first published on 01 May 2008


Article type: Paper
DOI: 10.1039/B719992A
Citation: Green Chem., 2008,10, 647-653
  •   Request permissions

    Stereoselective oxidation of R-(+)-limonene by chloroperoxidase from Caldariomyces fumago

    S. Águila, R. Vazquez-Duhalt, R. Tinoco, M. Rivera, G. Pecchi and J. B. Alderete, Green Chem., 2008, 10, 647
    DOI: 10.1039/B719992A

Search articles by author

Spotlight

Advertisements