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25-Hydroxyvitamin D3 Synthesis by Enzymatic Steroid Side-Chain Hydroxylation with Water.
- Source :
-
Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2016 Jan 26; Vol. 55 (5), pp. 1881-4. Date of Electronic Publication: 2015 Dec 22. - Publication Year :
- 2016
-
Abstract
- The hydroxylation of vitamin D3 (VD3, cholecalciferol) side chains to give 25-hydroxyvitamin D3 (25OHVD3) is a crucial reaction in the formation of the circulating and biologically active forms of VD3 . It is usually catalyzed by cytochrome P450 monooxygenases that depend on complex electron donor systems. Cell-free extracts and a purified Mo enzyme from a bacterium anaerobically grown with cholesterol were employed for the regioselective, ferricyanide-dependent hydroxylation of VD3 and proVD3 (7-dehydrocholesterol) into the corresponding tertiary alcohols with greater than 99 % yield. Hydroxylation of VD3 strictly depends on a cyclodextrin-assisted isomerization of VD3 into preVD3 , the actual enzymatic substrate. This facile and robust method developed for 25OHVD3 synthesis is a novel example for the concept of substrate-engineered catalysis and offers an attractive alternative to chemical or O2 /electron-donor-dependent enzymatic procedures.<br /> (© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.)
- Subjects :
- Hydroxylation
Water chemistry
Cholecalciferol chemical synthesis
Steroids chemistry
Subjects
Details
- Language :
- English
- ISSN :
- 1521-3773
- Volume :
- 55
- Issue :
- 5
- Database :
- MEDLINE
- Journal :
- Angewandte Chemie (International ed. in English)
- Publication Type :
- Academic Journal
- Accession number :
- 26695374
- Full Text :
- https://doi.org/10.1002/anie.201510331