Journal
CHEMCATCHEM
Volume 7, Issue 2, Pages 283-290Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cctc.201402795
Keywords
biocatalysis; hydroxylation; peroxygenase; regioselectivity; vitamins
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Funding
- INDOX [KBBE-2013-7-613549]
- EU
- HIPOP f the Spanish Ministry of Economy and Competitiveness [BIO2011-26694]
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Monohydroxylated metabolites of vitamin D-3 (cholecalciferol) and vitamin D-2 (ergocalciferol), generically known as 25-hydroxycalciferol, are better for several diseases, and other applications, than vitamin D (calciferol). This work describes a novel biotechnological approach for the preparation of 25-hydroxycalciferols, starting from readily available cholecalciferol and ergocalciferol. This approach enables the regioselective (100%) hydroxylation of these compounds (at the C-25 position) under mild and environmentally friendly conditions by using a peroxidase from the fungus Coprinopsis cinerea (gene model CC1G_08427T0 from the sequenced genome), which catalyzes monooxygenation with H2O2 as the only co-substrate (peroxygenase). Hydroxylation of cholecalciferol and ergocalciferol is a true peroxygenation, as demonstrated by incorporation of O-18 from H-2 O-18(2) into the products. The peroxygenase has additional advantages related to its recombinant nature, enabling enzyme engineering and low-cost overexpression in an industrial host. Therefore, the peroxygenase is a promising biocatalyst for the production of vitamin D active metabolites.
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