Synthesis of 2α-propoxy-1α,25-dihydroxyvitamin D3 and comparison of its metabolism by human CYP24A1 and rat CYP24A1

Nozomi Saito, Yoshitomo Suhara, Daisuke Abe, Tatsuya Kusudo, Miho Ohta, Kaori Yasuda, Toshiyuki Sakaki, Shinobu Honzawa, Toshie Fujishima, Atsushi Kittaka

Research output: Contribution to journalArticle

19 Citations (Scopus)

Abstract

A new vitamin D3 analogue, 2α-propoxy-1α,25-dihydroxyvitamin D3 (C3O1), was synthesized starting from d-glucose as a chiral template of the A-ring with a CD-ring bromoolefin unit using the Trost coupling method. We studied the metabolism of the new analogue by human CYP24A1 and rat CYP24A1 to learn of species-based differences and found that the former has multiple metabolic pathways, but the latter has only a single pathway.

Original languageEnglish
Pages (from-to)4296-4301
Number of pages6
JournalBioorganic and Medicinal Chemistry
Volume17
Issue number13
DOIs
Publication statusPublished - 2009 Jul 1

Keywords

  • Human CYP24A1
  • Metabolism
  • Rat CYP24A1
  • Vitamin D analogues

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

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    Saito, N., Suhara, Y., Abe, D., Kusudo, T., Ohta, M., Yasuda, K., Sakaki, T., Honzawa, S., Fujishima, T., & Kittaka, A. (2009). Synthesis of 2α-propoxy-1α,25-dihydroxyvitamin D3 and comparison of its metabolism by human CYP24A1 and rat CYP24A1. Bioorganic and Medicinal Chemistry, 17(13), 4296-4301. https://doi.org/10.1016/j.bmc.2009.05.032