Department of Chemistry, Tokyo Institute of Technology, O-okayama, Meguro-ku, Tokyo, 152 Japan.
Proc Natl Acad Sci U S A. 1981 Nov;78(11):6579-83. doi: 10.1073/pnas.78.11.6579.
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-[3alpha-(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-[3alpha-(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 (23S,25R)-25-hydroxyvitamin D(3) 26,23-lactone, establishing it as the natural vitamin D(3) metabolite.
四种立体异构体的 25-羟基维生素 D(3)26,23-内酯通过立体选择性内酯化方法合成。天然 25-羟基维生素 D(3)26,23-内酯由 25-羟基-[3alpha-(3)H]维生素 D(3)通过体外孵育维生素 D 补充鸡的肾匀浆或从给予 1,25-二羟基维生素 D(3)和 25-羟基-[3alpha-(3)H]维生素 D(3)的大鼠血清中分离出来。四种合成异构体和天然产生的 25-羟基维生素 D(3)26,23-内酯在能够分离四种异构体的高效液相色谱系统中进行分析。天然内酯与合成的(23S,25R)-25-羟基维生素 D(3)26,23-内酯共迁移,确定其为天然维生素 D(3)代谢物。