Chemoselective chloroperoxidase-catalyzed oxidation of hexen-1-ols

Author: Lindborg Jutta   Tanskanen Annukka   Kanerva Liisa  

Publisher: Informa Healthcare

ISSN: 1024-2422

Source: Biocatalysis and Biotransformation, Vol.27, Iss.3, 2009-05, pp. : 204-210

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Abstract

The chemoselectivity of chloroperoxidase from Caldariomyces fumago has been studied for the oxidation of cis- and trans-hexen-1-ols with tert-butyl hydroperoxide in a two-phase system of hexane or cyclohexane and citrate buffer (4:1, v/v; pH 5.0 ). In the hexen-1-ols used, the position of the C = C bond varied systematically from position 2 to position 5. According to GC analysis, the main oxidation product was always the corresponding aldehyde, and the epoxidation product was seen only in the case of 4-hexen-1-ols. For trans-4-hexen-1-ol, the amount of detectable oxidation products generally stayed extremely low although the alcohol itself disappeared smoothly with time, suggesting extensive condensation/ring opening as further reactions of the produced aldehyde and epoxyalcohol.