Synthesis of Acetylimino Linked Thymidine Dimers

• Main Authors: Fang-Chi Chien, 簡芳祺
• Other Authors: Te-Fang Yang
• Format: Others
• Language: zh-TW
• Published: 2000
• Online Access: http://ndltd.ncl.edu.tw/handle/37188695495787192250

碩士 === 朝陽大學 === 應用化學系碩士班 === 88 === 英文摘要： Nucleoside dimers containing synthetic amide, carbamate or methylene methylimino linkage instead of natural phosphodiester backbone have shown their incorporation into antisense oligonucleotide sequences which are potential antitumer and antiviral agents. Thus, in order to further study and improve the biological and physical properties of antisense oligonucleotides, we are interested in the synthesis of nucleoside dimer containing oxime、hydroxylamine and acetylimino linkages which are individually a part of various oligonucleotides. Thymidine is the starting material. Some of the imtermediates are 3''-O-amino-thymidine, 5''-O-amino-thymidine, 3''-oxothymidine and 5''-formylthymidine. Thymidine dimer containing imino linkage will be first synthesized. Acetylation of imino linkage provides acetylimino linkage by which two thymidine molecules are connected. The final products are thymidine dimer individually containing (3’-N →5’-O-) oxime, (3’-N →5’-O-) hydroxylamine (3’-N→5’-O-) acetylimino linkages. and (5’-N→3’-O-) oxime (5’-N→3’-O) hydroxylamine (5’-N→3’-O) acetylimino linkages.