维生素D化合物的直接C-1羟基化：1α-羟基维生素D3、1α,25-二羟基维生素D3和1α-羟基维生素D2的简便制备
Direct C-1 hydroxylation of vitamin D compounds: convenient preparation of 1alpha-hydroxyvitamin D3, 1alpha, 25-dihydroxyvitamin D3, and 1alpha-hydroxyvitamin D2.
作者信息
Paaren H E, Hamer D E, Schnoes H K, DeLuca H F
出版信息
Proc Natl Acad Sci U S A. 1978 May;75(5):2080-1. doi: 10.1073/pnas.75.5.2080.
Abstract
An efficient procedure for the direct C-1 hydroxylation of vitamin D compounds has been developed. The method involves conversion of vitamin D3 tosylates to 3,5-cyclovitamin D derivatives, allylic oxidation with selenium dioxide, and acid-catalyzed solvolysis to the 1 alpha-hydroxyvitamin D analogs. When applied to vitamin D3,25-hydroxyvitamin D3, and vitamin D2, this sequence give the corresponding 1alpha-hydroxylated derivatives in 10-15% yield.
摘要
已开发出一种用于维生素D化合物直接C-1羟基化的有效方法。该方法包括将维生素D3甲苯磺酸盐转化为3,5-环维生素D衍生物，用二氧化硒进行烯丙基氧化，以及酸催化溶剂解为1α-羟基维生素D类似物。当应用于维生素D3、25-羟基维生素D3和维生素D2时，该序列以10-15%的产率得到相应的1α-羟基化衍生物。
相似文献
1
Direct C-1 hydroxylation of vitamin D compounds: convenient preparation of 1alpha-hydroxyvitamin D3, 1alpha, 25-dihydroxyvitamin D3, and 1alpha-hydroxyvitamin D2.维生素D化合物的直接C-1羟基化：1α-羟基维生素D3、1α,25-二羟基维生素D3和1α-羟基维生素D2的简便制备
Proc Natl Acad Sci U S A. 1978 May;75(5):2080-1. doi: 10.1073/pnas.75.5.2080.
2
1 alpha-hydroxylation of 24-hydroxyvitamin D2 represents a minor physiological pathway for the activation of vitamin D2 in mammals.
Biochemistry. 1990 Jan 16;29(2):578-82. doi: 10.1021/bi00454a035.
3
Radioligand receptor assay for 25-hydroxyvitamin D2/D3 and 1 alpha, 25-dihydroxyvitamin D2/D3.25-羟维生素D2/D3和1α,25-二羟维生素D2/D3的放射性配体受体测定
J Clin Invest. 1976 Jul;58(1):61-70. doi: 10.1172/JCI108459.
4
Evidence for the activation of 1alpha-hydroxyvitamin D2 by 25-hydroxyvitamin D-24-hydroxylase: delineation of pathways involving 1alpha,24-dihydroxyvitamin D2 and 1alpha,25-dihydroxyvitamin D2.25-羟基维生素D-24-羟化酶激活1α-羟基维生素D2的证据：涉及1α,24-二羟基维生素D2和1α,25-二羟基维生素D2的途径的描述
Biochim Biophys Acta. 2006 Feb;1761(2):221-34. doi: 10.1016/j.bbalip.2006.01.004. Epub 2006 Feb 2.
5
6
Metabolism of vitamin D in patients with primary biliary cirrhosis and alcoholic liver disease.原发性胆汁性肝硬化和酒精性肝病患者的维生素D代谢
Clin Sci (Lond). 1985 Nov;69(5):561-70. doi: 10.1042/cs0690561.
7
1 Alpha-hydroxyvitamin D2 and 1 alpha-hydroxyvitamin D3 have anabolic effects on cortical bone, but induce intracortical remodeling at toxic doses in ovariectomized rats.1α-羟基维生素D2和1α-羟基维生素D3对皮质骨具有合成代谢作用，但在去卵巢大鼠中，高剂量时会诱导皮质内重塑。
Bone. 2004 Sep;35(3):704-10. doi: 10.1016/j.bone.2004.04.011.
8
Evaluation of the total fetomaternal vitamin D relationships at term: evidence for racial differences.足月时胎儿与母体维生素D总量关系的评估：种族差异的证据
J Clin Endocrinol Metab. 1984 Oct;59(4):652-7. doi: 10.1210/jcem-59-4-652.
9
The estimation of vitamin D and some metabolites in human plasma by mass fragmentography.用质量碎片谱法测定人体血浆中的维生素D及某些代谢物。
Clin Chim Acta. 1980 Sep 8;106(1):51-62. doi: 10.1016/0009-8981(80)90374-5.
10
An efficient synthesis of 1α,25-dihydroxyvitamin D LC-biotin.1α,25-二羟基维生素D LC-生物素的高效合成。
J Steroid Biochem Mol Biol. 2017 Oct;173:89-92. doi: 10.1016/j.jsbmb.2017.01.025. Epub 2017 Feb 6.
引用本文的文献
1
The vitamin D hormone, 1,25(OH)D, regulates fibroblast growth factor 23 (FGF23) production in human skin cells.维生素D激素1,25(OH)D可调节人类皮肤细胞中成纤维细胞生长因子23（FGF23）的生成。
Am J Physiol Cell Physiol. 2025 Apr 1;328(4):C1177-C1192. doi: 10.1152/ajpcell.00827.2024. Epub 2025 Mar 7.
2
Comparison of Bioavailability of 1-Hydroxycholecalciferol and Cholecalciferol in Broiler Chicken Diets.1-羟基胆钙化醇与胆钙化醇在肉鸡日粮中的生物利用度比较
J Poult Sci. 2016 Jan 25;53(1):22-28. doi: 10.2141/jpsa.0150009.
3
Construction of a P450c27 fusion enzyme: a useful tool for analysis of vitamin D3 25-hydroxylase activity.P450c27融合酶的构建：用于分析维生素D3 25-羟化酶活性的有用工具。
Biochem J. 1996 Nov 15;320 ( Pt 1)(Pt 1):267-71. doi: 10.1042/bj3200267.
本文引用的文献
1
1alpha-Hydroxyvitamin D2: a potent synthetic analog of vitamin D2.
Science. 1974 Dec 13;186(4168):1038-40. doi: 10.1126/science.186.4168.1038.
2
Conformational equilibria in vitamin D. Synthesis of 1beta-hydroxyvitamin D3.
J Org Chem. 1977 Oct 28;42(22):3597-9. doi: 10.1021/jo00442a033.
3
The selenium dioxide oxidation of cholecalciferol.
Steroids. 1977 Aug;30(2):193-201. doi: 10.1016/0039-128x(77)90081-2.
4
Metabolism and mechanism of action of vitamin D.
Annu Rev Biochem. 1976;45:631-66. doi: 10.1146/annurev.bi.45.070176.003215.
5
Letter: The vitamin D-3,5-cyclovitamin D rearrangement.
J Am Chem Soc. 1975 Oct 15;97(21):6249-50. doi: 10.1021/ja00854a053.
Zotero 插件