Stereo-retained and stereo-selective lactonization of four diastereoisomers of 23,25,26-trihydroxyvitamin D3 in homogenates of kidney from vitamin D-supplemented chicks.
To elucidate the biosynthesis of 25-hydroxyvitamin D3-26,23-lactone, various vitamin D3 derivatives were incubated individually with kidney homogenates prepared from vitamin D3-supplemented chicks, a preparation known to produce the 25-hydroxyvitamin D3-26,23-lactone from 25-hydroxyvitamin D3. The 25-hydroxyvitamin D3-26, 23-lactone produced in vitro was then separated, purified, identified, and quantitated by consecutive analysis by high-pressure liquid chromatography. The naturally occurring 23(S), 25(R)-25-hydroxyvitamin D3-26,23-lactone was produced from 23(S),25-dihydroxyvitamin D3, 25(R),26-dihydroxyvitamin D3, and 23(S),25(R),26-trihydroxyvitamin D3. 23(S),25 (S)-25-Hydroxyvitamin D3-26,23-lactone was synthesized from 25(S),26-dihydroxyvitamin D3 and 23(S),25(S),26-trihydroxyvitamin D3. The relative amounts of 25-hydroxyvitamin D3-26,23-lactones generated from the following vitamin D3 derivatives used as substrate (23(S),25(S),26-trihydroxyvitamin D3; 23(R),25(R),26-trihydroxyvitamin D3; 23(S),25(R),26-trihydroxyvitamin D3; 23(R),25(S),26-trihydroxyvitamin D3; 23(S), 25-dihydroxyvitamin D3; 23(R),25-dihydroxyvitamin D3; 25(S),26-dihydroxyvitamin D3; and 25(R),26-dihydroxyvitamin D3) are, respectively, 15:1.7:24:3.3:2.5:0:1:1.7. These results indicate that when the lactonization at C-23 and C-26 positions of various vitamin D3 derivatives occurred the stereochemical configuration at their C-23 and/or C-25 positions was not changed and the difference of the stereochemical configurations determined the rate of lactonization.
D000818:Animals; D002112:Calcifediol / Q000031:analogs & derivatives* / Q000096:biosynthesis; D002117:Calcitriol / Q000494:pharmacology*; D002645:Chickens; D002851:Chromatography, High Pressure Liquid; D004100:Dihydroxycholecalciferols / Q000378:metabolism; D006887:Hydroxycholecalciferols / Q000378:metabolism*; D007668:Kidney / Q000378:metabolism*; D008297:Male; D008968:Molecular Conformation; D013237:Stereoisomerism
D004100:Dihydroxycholecalciferols; D006887:Hydroxycholecalciferols; C026396:calcifediol lactone; C031699:23,25-dihydroxyvitamin D3; C034128:23,25,26-trihydroxyvitamin D3; D002117:Calcitriol; D002112:Calcifediol; C026032:25,26-dihydroxycholecalciferol