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Peroxygenase-catalysed selective and scalable synthesis of 25-hydroxy-grundmann's ketone and its derivatives.
- Source :
-
Molecular Catalysis . Aug2023, Vol. 547, pN.PAG-N.PAG. 1p. - Publication Year :
- 2023
-
Abstract
- • A new biocatalytic approach to convert Grundmann's Ketone and its derivatives. • Up to 99% conversion and regioselectivity enabled by peroxygenase. • Expanding the use of enzymes in the transformation of vitamin D related compounds. • Independence of NAD(P)H cofactors, easy scalability to 0.2 L reaction scale. Peroxygenases are selective catalysts for C-H bond oxyfunctionalization reactions, however, their potential for organic synthesis still needs to be explored. 25-Hydroxy-Grundmann's ketone is a key structural motifs in various biologically active vitamin D 3 analogues. In this study, we report the use of unspecific peroxygenase from Agrocybe aegerita as a highly selective catalyst for the C25 hydroxylation of Grundmanns's ketone and its analogues. Under the optimised conditions, excellent conversion (> 99%) and regioselectivity (> 99%) was obtained. The selected hydroxylation processes were performed on an increased lab scale (up to 200 mL) with up to 1 mmol substrate, which led in 85.7% isolated yield.This simple biocatalytic method holds great potential in streamlining the synthetic pathways of vitamin D 3 analogues. [Display omitted] [ABSTRACT FROM AUTHOR]
- Subjects :
- *KETONES
*HYDROXYLATION
*CHOLECALCIFEROL
*CATALYSTS
*CATALYSIS
Subjects
Details
- Language :
- English
- ISSN :
- 24688231
- Volume :
- 547
- Database :
- Academic Search Index
- Journal :
- Molecular Catalysis
- Publication Type :
- Academic Journal
- Accession number :
- 169753870
- Full Text :
- https://doi.org/10.1016/j.mcat.2023.113389