碩士 / 國立交通大學 / 應用化學系分子科學碩博士班 / 104 / Amino sugars are widely existed in natural products, such as lipopolysaccharides, glycolipids, nucleotides, and antibiotics. It can involved in many biological functions, such as immune modulation, cell recognition; therefore, chemical synthesis of aminosugar-containing oligosaccharides are more important issue.
4-amino-4,6-dideoxy-Galp are mostly existed in lipopolysaccharides of bacteria, such as lipopolysaccharides of Treponema medium、lipopolysaccharides IV of M. marinum. 4-amino-4,6-dideoxy-Galp usually linked with glycosyl residues by 1,2-cis glycosidic linkages to form polysaccharides. We employed a NFM-modulating glycosylation and a novel iterative modulating glycosylation for 4-azido-4,6-dideoxy- thiogalactoglycosides with different glycosyl acceptors to construct 1,2-cis glycosides. The novel iterative modulating glycosylation provide a mild and convenient entry without protecting group manipulation to be able to afford high 1,2 cis-selectivity.
M. marinum LOS-IV is terminated with a family of N-acylated 4-amino-4,6-dideoxygalactopyranose residues which contain a pyrrolidone group, Za, Zb and Zc. We also try to synthesize angulous pyrrolidone group which is resembled natural pyrrolidone group, Zb, in M. marinum LOS-IV. We also extended NFM-modulating glycosylation toward synthesis of oligosaacharide fragments of Mycobacterium marinum lipooligosaaccharide IV.
| Identifer | oai:union.ndltd.org:TW/104NCTU5309004 |
| Date | January 2015 |
| Creators | Chang, Bo-Yao, 張博堯 |
| Contributors | Mong, Kwok-Kong, 蒙國光 |
| Source Sets | National Digital Library of Theses and Dissertations in Taiwan |
| Language | zh-TW |
| Detected Language | English |
| Type | 學位論文 ; thesis |
| Format | 152 |
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