*Please refer to dissertation for diagrams. / In this thesis, a review concerning enantiospecific syntheses and structure activity relationship of N-linked carbadisaccharides from 1994 to 2005 is presented. / Valienamine was isolated from microbial degradation products of validoxylamine A with Pseudomonas denitrificans. It showed alpha-glycosidase inhibitory activity and antibiotic activity. Isopropylidene protected allylic chlorides, 2-epi-valienamine and 4-amino-6-deoxy-alpha- D-pseudomannopyranose were synthesized from (-)-quinic acid. The acetonide blocking groups were shown to be the best hydroxyl protecting groups for coupling precursors, compatible with palladium-catalyzed coupling reaction which afforded high yields of the 1,1'- and 1,4'-N-linked carbadisaccharides 83-88 and 89-91, respectively, with a minimum amount of an elimination diene side-product. 2-epi-Valienamines 92 and N-alkyl 2-epi-valienamine 93 and 94 were also prepared. The key palladium-catalyzed coupling reaction was shown to be a regio- and stereospecific reaction. Acid hydrolysis was used to obtain free pseudoaminosugars as glycosidase inhibitors. The inhibitory activities of these pseudoaminosugars were evaluated by the Biochemistry Department of the Chinese University of Hong Kong.* / Kwong Suk Kwan. / "January 2006." / Adviser: Tony K. M. Shing. / Source: Dissertation Abstracts International, Volume: 67-11, Section: B, page: 6409. / Thesis (Ph.D.)--Chinese University of Hong Kong, 2006. / Includes bibliographical references (p. 146-154). / Electronic reproduction. Hong Kong : Chinese University of Hong Kong, [2012] System requirements: Adobe Acrobat Reader. Available via World Wide Web. / Electronic reproduction. [Ann Arbor, MI] : ProQuest Information and Learning, [200-] System requirements: Adobe Acrobat Reader. Available via World Wide Web. / Abstracts in English and Chinese. / School code: 1307.
| Identifer | oai:union.ndltd.org:cuhk.edu.hk/oai:cuhk-dr:cuhk_343725 |
| Date | January 2006 |
| Contributors | Kwong, Suk Kwan., Chinese University of Hong Kong Graduate School. Division of Chemistry. |
| Source Sets | The Chinese University of Hong Kong |
| Language | English, Chinese |
| Detected Language | English |
| Type | Text, theses |
| Format | electronic resource, microform, microfiche, 1 online resource (xii, 156, [139] p. : ill.) |
| Rights | Use of this resource is governed by the terms and conditions of the Creative Commons “Attribution-NonCommercial-NoDerivatives 4.0 International” License (http://creativecommons.org/licenses/by-nc-nd/4.0/) |
Page generated in 0.002 seconds