Synthesis of galactosyltransferase inhibitors from sugar lactones

• Main Authors: Yueh-chiang Han, 韓岳強
• Other Authors: Chun-hung Lin
• Format: Others
• Language: zh-TW
• Published: 2002
• Online Access: http://ndltd.ncl.edu.tw/handle/65226051703086144848

碩士 === 國立臺灣大學 === 生化科學研究所 === 90 === Galactosyltransferases play an essential role in many living organisms. The biosynthesis of many important glycoconjugates are catalyzed by the enzymes and other glycosyltransferases. Thus, the development of corresponding enzyme inhibitors is of current interest as these molecules may be used as either the regulators to control cellular behaviors, or potent therapeutic drugs. According to our previous result in sugar lactone chemistry, sugar-phosphonate was generated by nucleophilic addition and subsequent dehydration. However, the synthetic strategy had to be modified due to the unsuccessful deprotection of p-methoxy benzyl and allyl groups. The preparation of precursor 12 from 1-hydroxy-a-D- galactonopyranose-1-methyl-phosphonic acid (11) was failed probably owing to the solubility problem. The coupling reaction of 1-hydroxy-2, 3, 4, 6-tetra-O-benzyl-a-D-galactonopyranose-1- methyl-phosphonic acid (15) and UMP-morpholidate was not accomplished either. We proposed that failure might arise from the different conformation of sugar-phosphonate from that of sugar-phosphate. As a consequence, we planed to synthesize UDP-galactose.