by Stanton Hon-Lung Kok. / Thesis (Ph.D.)--Chinese University of Hong Kong, 1999. / Includes bibliographical references (p. 142-147). / Electronic reproduction. Hong Kong : Chinese University of Hong Kong, [2012] System requirements: Adobe Acrobat Reader. Available via World Wide Web. / Mode of access: World Wide Web. / Abstracts in English and Chinese.

Cheung Wai-chit. / "July 2004." / Thesis (Ph.D.)--Chinese University of Hong Kong, 2004 / Includes bibliographical references (p. 135-140) / Electronic reproduction. Hong Kong : Chinese University of Hong Kong, [2012] System requirements: Adobe Acrobat Reader. Available via World Wide Web. / Mode of access: World Wide Web. / Abstracts in English and Chinese.

*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.

[Truncated abstract] The development of several carbohydrate-based pharmaceuticals has stimulated an increased interest in the field of carbohydrate chemistry. The discovery of Acarbose and invention of Miglitol, treatments for type II diabetes, as well as the influenza treatments, Relenza and Tamiflu, have been largely responsible for this increased interest. These treatments operate by the inhibition of glycoside hydrolases, a group of enzymes important in a variety of biological processes. This thesis involves the study of a group of glycoside hydrolase inhibitors known as azasugars, which are nitrogen-containing sugar mimics . . . The final chapter, Chapter 4, focuses on the testing of these disaccharides as a possible alternative carbohydrate source for pre-term infants. Initially, commercially available glycoside hydrolases were used to detect any hydrolysis of the four disaccharides, with (206) exhibiting the most promising results (to provide D-glucose and D-galactose). Detailed kinetic studies were then conducted using homogenates obtained from pig intestinal mucosa. Unfortunately, the results indicated that (206) was unsuitable as an alternative carbohydrate source for pre-term infants.

by Lee Chi-Chung. / Thesis (M.Phil.)--Chinese University of Hong Kong, 2001. / Includes bibliographical references (leaves 74-78). / Abstracts in English and Chinese. / Acknowledgment --- p.ii / Table of Contents --- p.iii / Abstract --- p.v / Abstract (Chinese Version) --- p.vi / Abbreviation --- p.vii / Chapter 1. --- Introduction --- p.1 / Chapter 1.1 --- General Background --- p.1 / Chapter 1.1.1 --- Valienamine --- p.2 / Chapter 1.1.2 --- Valienamine Derivatives --- p.4 / Chapter 1.2 --- Mechanistic Aspects of Glycosidase Inhibition --- p.6 / Chapter 1.2.1 --- General Background --- p.6 / Chapter 1.2.2 --- Mechanism of Enzyme Catalyzed Hydrolysis of Glycosides --- p.6 / Chapter 1.2.3 --- Types of Glucosidase Inhibitors --- p.7 / Chapter 1.2.4 --- Inhibition of Glycosidases by Valienamine Derivatives --- p.8 / Chapter 1.3 --- Previous Synthesis of Valienamine --- p.9 / Chapter 1.3.1 --- Enantiospecific Synthesis of Valienamine by Vasella and co-workers --- p.9 / Chapter 1.3.2 --- Enantiospecific Synthesis of Valienamine by Tatsuta and co-workers --- p.10 / Chapter 1.3.3 --- Synthesis of N-Alkyl Derivatives of Valienamine --- p.12 / Chapter 1.4 --- Previous Syntheses of Valienamine-containing Pseudodisaccharides and its Diastereomers --- p.12 / Chapter 1.4.1 --- Epoxide aminolysis --- p.12 / Chapter 1.4.2 --- Condensation of amine with ketone --- p.15 / Chapter 1.4.3 --- Synthesis of pseudoaminodisaccharide by Kapp and co-workers --- p.16 / Chapter 2. --- Results and Discussion --- p.18 / Chapter 2.1 --- General Strategy --- p.18 / Chapter 2.2 --- Syntheses of coupling precursors --- p.20 / Chapter 2.2.1 --- Syntheses of protected valienamine 65 and its 2-epimer80 --- p.20 / Chapter 2.2.1.1 --- Synthesis of Diol68 --- p.20 / Chapter 2.2.1.2 --- Synthesis of Diol67 --- p.21 / Chapter 2.2.1.3 --- Synthesis of protected valienamine 65 and its 2-epimer80 --- p.22 / Chapter 2.2.2 --- Syntheses of 6-deoxyaminosugars 63 and118 --- p.24 / Chapter 2.2.2.1 --- Synthesis of benzyl ether91 --- p.24 / Chapter 2.2.2.2 --- Synthesis of β-diol103 --- p.28 / Chapter 2.2.2.3 --- Synthesis of α-alcohol107 --- p.30 / Chapter 2.2.2.4 --- Synthesis of β-diol113 --- p.31 / Chapter 2.2.2.5 --- Syntheses of amines 63 and118 --- p.33 / Chapter 2.2.3 --- Syntheses of allylic chlorides --- p.34 / Chapter 2.3 --- Syntheses of pseudoaminodissaccharides --- p.36 / Chapter 3. --- Conclusion --- p.42 / Chapter 4. --- Experimental --- p.44 / Chapter 5. --- References --- p.74 / Chapter 6. --- Appendix --- p.79 / List of spectra --- p.79