Synthesis of 2alpha-propoxy-1alpha,25-dihydroxyvitamin D3 and comparison of its metabolism by human CYP24A1 and rat CYP24A1.
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.
Saito
Nozomi
N
Faculty of Pharmaceutical Sciences, Teikyo University, Sagamiko, Sagamihara, Kanagawa, Japan.
Suhara
Yoshitomo
Y
Abe
Daisuke
D
Kusudo
Tatsuya
T
Ohta
Miho
M
Yasuda
Kaori
K
Sakaki
Toshiyuki
T
Honzawa
Shinobu
S
Fujishima
Toshie
T
Kittaka
Atsushi
A
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
C118756:dihydroxy-vitamin D3; D014807:Vitamin D; D013250:Steroid Hydroxylases; C585549:CYP24A1 protein, human; C585551:Cyp24a1 protein, rat; D065668:Vitamin D3 24-Hydroxylase