A new suprasterol by photochemical reaction of 1α,25-dihydroxy-9-methylene-19-norvitamin D3

Urszula Kulesza; Lori A. Plum; Hector F. DeLuca; Antonio Mouriño; Rafal R. Sicinski

doi:10.1039/C5OB01896J

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A new suprasterol by photochemical reaction of 1α,25-dihydroxy-9-methylene-19-norvitamin D₃†

Urszula Kulesza,^ab Lori A. Plum,^c Hector F. DeLuca,^c Antonio Mouriño

*^b and Rafal R. Sicinski*^a

Author affiliations

* Corresponding authors

^a Faculty of Chemistry, University of Warsaw, Pasteura 1, 02-093 Warsaw, Poland
E-mail: rasici@chem.uw.edu.pl

^b Departamento de Química Orgánica, Laboratorio de Investigación Ignacio Ribas, Universidad de Santiago de Compostela, Avda. Ciencias s/n, 15782 Santiago de Compostela, Spain
E-mail: antonio.mourino@usc.es

^c Department of Biochemistry, University of Wisconsin-Madison, 433 Babcock Drive, Madison, WI 53706, USA

Abstract

The UV-induced photochemical reaction of 1α,25-dihydroxy-9-methylene-19-norvitamin D₃ has been investigated. The pentacyclic structure of the isolated product has been unequivocally established by X-ray crystallographic analysis. The possible reaction paths of the examined photochemical transformation are discussed. Biological in vivo and in vitro tests proved that the photoproduct is devoid of calcemic activity.

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Article information

DOI: https://doi.org/10.1039/C5OB01896J
Article type: Paper
Submitted: 11 Sep 2015
Accepted: 09 Dec 2015
First published: 09 Dec 2015

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Org. Biomol. Chem., 2016,14, 1646-1652

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A new suprasterol by photochemical reaction of 1α,25-dihydroxy-9-methylene-19-norvitamin D₃

U. Kulesza, L. A. Plum, H. F. DeLuca, A. Mouriño and R. R. Sicinski, Org. Biomol. Chem., 2016, 14, 1646 DOI: 10.1039/C5OB01896J

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Organic & Biomolecular Chemistry