Synthesis and determination of configuration of natural 25-hydroxyvitamin D 3 26,23-lactone

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Abstract
The four stereoisomers of 25-hydroxyvitamin D 3 26,23-lactone were synthesized by a stereoselective lactonization method. Natural 25-hydroxyvitamin D 3 26,23-lactone was produced from 25-hydroxy-[3α- 3 H]vitamin D 3 by in vitro incubation of kidney homogenate prepared from vitamin D-supplemented chickens or was isolated from the serum of rats given 1,25-dihydroxyvitamin D 3 and 25-hydroxy-[3α- 3 H]vitamin D 3 . The four synthetic isomers and the naturally produced 25-hydroxyvitamin D 3 26,23-lactone were subjected to high-performance liquid chromatography in a system capable of separating the four isomers. The natural lactone comigrated with synthetic (23 S ,25 R )-25-hydroxyvitamin D 3 26,23-lactone, establishing it as the natural vitamin D 3 metabolite.