Literature DB >> 30367940

Concise synthesis of 23-hydroxylated vitamin D3 metabolites.

Fumihiro Kawagoe1, Toru Sugiyama2, Kaori Yasuda3, Motonari Uesugi4, Toshiyuki Sakaki3, Atsushi Kittaka5.   

Abstract

Three 23-hydroxylated vitamin D3 derivatives, which are metabolites of 25-hydroxyvitamin D3 produced by CYP24A1 and a related diastereomer, were efficiently synthesized. Each C23 hydroxy unit was constructed by the Claisen condensation reaction with ethyl acetate or the Grignard reaction with 2-methylallymagnesium chloride. Stereochemistry at the C23 position was determined by a modified Mosher's method. The triene structures were constructed by the Wittig-Horner reaction utilizing the A-ring phosphine oxide moiety.
Copyright © 2018 Elsevier Ltd. All rights reserved.

Entities:  

Keywords:  23-Hydroxyvitamin D(3); Modified Mosher’s method; Synthesis; Vitamin D(3) metabolite

Mesh：

Substances：

Year:  2018        PMID： 30367940     DOI： 10.1016/j.jsbmb.2018.10.010

Source DB:  PubMed          Journal:  J Steroid Biochem Mol Biol        ISSN： 0960-0760            Impact factor:   4.292


  3 in total

1.  Elucidation of metabolic pathways of 25-hydroxyvitamin D3 mediated by Cyp24a1 and Cyp3a using Cyp24a1 knockout rats generated by CRISPR/Cas9 system.

Authors:  Kaori Yasuda; Miyu Nishikawa; Kairi Okamoto; Kyohei Horibe; Hiroki Mano; Mana Yamaguchi; Risa Okon; Kimie Nakagawa; Naoko Tsugawa; Toshio Okano; Fumihiro Kawagoe; Atsushi Kittaka; Shinichi Ikushiro; Toshiyuki Sakaki
Journal:  J Biol Chem       Date:  2021-04-15       Impact factor: 5.157

2.  Stereoselective Synthesis of 24-Fluoro-25-Hydroxyvitamin D3 Analogues and Their Stability to hCYP24A1-Dependent Catabolism.

Authors:  Fumihiro Kawagoe; Sayuri Mototani; Kaori Yasuda; Hiroki Mano; Toshiyuki Sakaki; Atsushi Kittaka
Journal:  Int J Mol Sci       Date:  2021-11-01       Impact factor: 5.923

Review 3.  Development of In Vitro and In Vivo Evaluation Systems for Vitamin D Derivatives and Their Application to Drug Discovery.

Authors:  Kaori Yasuda; Miyu Nishikawa; Hiroki Mano; Masashi Takano; Atsushi Kittaka; Shinichi Ikushiro; Toshiyuki Sakaki
Journal:  Int J Mol Sci       Date:  2021-10-31       Impact factor: 5.923
  3 in total

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