全反式视黄醇β-D-葡萄糖醛酸苷的化学合成及促生长活性
Chemical synthesis and growth-promoting activity of all-trans-retinyl beta-D-glucuronide.
作者信息
Barua A B, Olson J A
机构信息
Department of Biochemistry and Biophysics, Iowa State University, Ames 50011.
出版信息
Biochem J. 1987 May 15;244(1):231-4. doi: 10.1042/bj2440231.
All-trans-retinol reacts with methyl (2,3,4-tri-O-acetyl-1-bromo-1-deoxy-beta-D-glucopyran)uronate in the presence of Ag2CO3 to give the triacetate methyl ester of retinyl beta-glucuronide. Hydrolysis of this ester with sodium methylate in methanol gives retinyl beta-D-glucuronide in about 15% yield. The water-soluble retinyl beta-D-glucuronide was characterized by u.v.-visible, n.m.r. and mass spectra, by elemental analysis and by its susceptibility to hydrolysis by bacterial beta-glucuronidase. Retinyl beta-glucuronide, when administered intraperitoneally in saline (0.9% NaCl), supports well the growth of vitamin A-deficient rats.
全反式视黄醇在碳酸银存在下与甲基（2,3,4-三-O-乙酰基-1-溴-1-脱氧-β-D-吡喃葡萄糖）uronate反应，生成视黄醇β-葡萄糖醛酸苷的三乙酸甲酯。该酯在甲醇中用甲醇钠水解，以约15%的产率得到视黄醇β-D-葡萄糖醛酸苷。水溶性视黄醇β-D-葡萄糖醛酸苷通过紫外可见光谱、核磁共振光谱和质谱、元素分析以及其对细菌β-葡萄糖醛酸酶水解的敏感性进行表征。视黄醇β-葡萄糖醛酸苷以生理盐水（0.9% NaCl）腹腔注射给药时，能很好地支持维生素A缺乏大鼠的生长。
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