title: Synthesis of 2alpha-propoxy-1alpha,25-dihydroxyvitamin D3 and comparison of its metabolism by human CYP24A1 and rat CYP24A1.
abstract: A new vitamin D(3) analogue, 2alpha-propoxy-1alpha,25-dihydroxyvitamin D(3) (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.
authors.affiliation: Faculty of Pharmaceutical Sciences, Teikyo University, Sagamiko, Sagamihara, Kanagawa, Japan.
authors.forename: Nozomi
authors.initials: N
authors.lastname: Saito
authors.forename: Yoshitomo
authors.initials: Y
authors.lastname: Suhara
authors.forename: Daisuke
authors.initials: D
authors.lastname: Abe
authors.forename: Tatsuya
authors.initials: T
authors.lastname: Kusudo
authors.forename: Miho
authors.initials: M
authors.lastname: Ohta
authors.forename: Kaori
authors.initials: K
authors.lastname: Yasuda
authors.forename: Toshiyuki
authors.initials: T
authors.lastname: Sakaki
authors.forename: Shinobu
authors.initials: S
authors.lastname: Honzawa
authors.forename: Toshie
authors.initials: T
authors.lastname: Fujishima
authors.forename: Atsushi
authors.initials: A
authors.lastname: Kittaka
mesh_terms: D000818:Animals; D002851:Chromatography, High Pressure Liquid; D004926:Escherichia coli / Q000235:genetics; D006801:Humans; D013058:Mass Spectrometry; D051381:Rats; D013250:Steroid Hydroxylases / Q000235:genetics / Q000378:metabolism*; D014807:Vitamin D / Q000031:analogs & derivatives* / Q000032:analysis / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism; D065668:Vitamin D3 24-Hydroxylase
chemical_list: C118756:dihydroxy-vitamin D3; D014807:Vitamin D; D013250:Steroid Hydroxylases; C585549:CYP24A1 protein, human; C585551:Cyp24a1 protein, rat; D065668:Vitamin D3 24-Hydroxylase