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Syntheses and Biochemical Evaluation of Novel Glycoligands

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Please use this identifier to cite or link to this item:https://doi.org/10.11501/3082564

Title: Syntheses and Biochemical Evaluation of Novel Glycoligands
Other Titles: 新しい糖鎖リガンドの合成と生化学的評価
Authors: Matsuoka, Koji1 Browse this author
Authors(alt): 松岡, 浩司1
Issue Date: 24-Mar-1995
Publisher: Hokkaido University
Abstract: Synthetic glycoconjugates as a novel class of useful tools for basic glycoscience studies were systematically designed and synthesized. The main purpose of this work was focused on creation of a new glycochemical field by hybridizing the conventional sugar-chemistry, polymer chemistry, and biochemistry. The thesis was composed of five chapters. The first chapter provided a general introduction to the roles of glycoconjugates in nature and the significance of molecular recognition based on the interaction of carbohydrates and proteins such as lectins and enzymes. ln order to investigate the structures and functions of a variety of glycoconjugates, it should be noted that we must consider some new strategy and methodology for the preparation of well characterized glycoligands and glycosubstrates in conjunction with glycobiology and glycoteclmology. ln the second chapter, facile and efficient syntheses of activated cyclic aldose derivatives were explained on the basis of a new combination of mercuric (II) bromide and 2,4,6-trimethylpyridine. Reactive intermediates such as orthoester and oxazoline derivatives synthesized here can be useful and versatile precursors for glycoconjugates syntheses and the application of these procedures will be discussed in following chapters. The third chapter under the title of "Glycoprotein Models: Polymeric Sugar Ligands Available for Determining The Binding Specificity of Lectins" gave a new strategy for the investigation of binding specificity of lectins with sugars using Polymeric glycoligands derived from a variety of polymerizable glycosides of N-acetyllactosamine and the related isomers. lt was clearly suggested that a lectin isolated from Erythrina collarodendron showed a specific affinity for β(1→4) type disaccharides and the precise evaluation of the interaction of carbohydrates and lectins can be firstly performed by means of polymeric sugar-cluster effect. Chapter 4 was devoted to the syntheses and biochemical evaluation of novel bi-fluorescence-labeled lactoside as a high performance substrate for ceramide glycanase isolated from leech (Macrobdella decora). This unique substrate prepared from n-pentenyl lactoside involved kind of fluorophores as a donor and an acceptor of fluorescence energy transfer in the molecule and showed two emission maximums at around 335 and 540 nm when the substrate was excited at 260 or 290 nm. Using a bi-fluorescence-labeled substrate for kinetic analysis in the enzyme reaction, the KM of the leech ceramide glycanase against the substrate was found to be 7.7 μM and the Vmax was determined to be 0.16 nmol/min. Concluding remarks will be described in Chapter 5.
Conffering University: 北海道大学
Degree Report Number: 甲第3550号
Degree Level: 博士
Degree Discipline: 理学
Type: theses (doctoral)
URI: http://hdl.handle.net/2115/51227
Appears in Collections:学位論文 (Theses) > 博士 (理学)

Submitter: 松岡 浩司

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