合成硫酸化N-乙醯乳醣胺及其衍伸物

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合成硫酸化N-乙醯乳醣胺及其衍伸物

Synthesis of N-acetyl Lactosamine Sulfates and Analogues

張琇琄 , Masters　　Advisor：姚清發;林俊宏　　

繁體中文

乙醯乳糖胺；硫酸化；醣基化；預活化； N-acetyllactosamine ； sulfation ； glycosylation. ； pre-activation

Abstract │ Reference (28) │ Altmetrics

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N-Acetyllactosamine (Gal-b-1,4-GlcNAc, LacNAc) and its 1,3-analogue often exist as repeating disaccharides resided at the non-reducing terminus of N-glycans. These carbohydrates are associated with numerous biological activities. For example, they are known to interact with various types of galectins for the immune-activity of B-cells. Recently the incorporation of sulfate groups to the hydroxyl group(s) was observed to greatly enhance the binding interaction with a variety of proteins. This thesis research aims at the synthesis of these sulfated Gal-1,3-GlcNAc, LacNAc and analogues in order for the purpose of systematic investigation. These target disaccharides were synthesized by the reactions steps of protecting group manipulations, glycosylation, selective deprotection and sulfation. We followed the previously established method to prepare the building blocks of Gal donor and GlcNAc-acceptor. The pre-activation method by using diphenyl sulfoxide-Tf2O was found to be suitable for formation of the desired b-1,3-linkage with satisfying high yields.

Reference ( 28 ) 〈TOP〉

1. Hughes, R. C., Galectins as modulators of cell adhesion. Biochimie 2001, 83, 667-676.
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2. Hikita, C.; Vijayakumar, S.; Takito, J.; Erdjument-Bromage, H.; Tempst, P.; Al-Awqati, Q., Induction of terminal differentiation in epithelial cells requires polymerization of hensin by galectin 3. J. Cell. Biol. 2000, 151, 1235-1246.
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3. Imberty, A.; Lortat-Jacob, H.; Perez, S., Structural view of glycosaminoglycan-protein interactions. Carbohydr. Res. 2007, 342, 430-439.
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4. Kjellen, L.; Lindahl, U., Proteoglycans - Structures and Interactions. Annu. Rev. Biochem. 1991, 60, 443-475.
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5. Capila, I.; Linhardt, R. J., Heparin - Protein interactions. Angew. Chem. Int. Ed. Engl. 2002, 41, 391-412.
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