藉由醣構築體反應性的不同來合成N-乙醯乳糖胺的四醣分子

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藉由醣構築體反應性的不同來合成N-乙醯乳糖胺的四醣分子

Synthesis of LacNAc Tetrasaccharide via a Reactivity-based Approach

蕭瑞甫 , Masters　　Advisor：林俊宏　　

繁體中文

交錯型保護基；相對反應性；一鍋化合成； N-乙醯乳醣胺；模組化合成； orthogonal protecting group ； RRV ； one-pot synthesis ； N-Acetyl lactosamine (LacNAc) ； modular synthesis

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Carbohydrates play an important role in numerous biological activities, including cell-cell interactions, recognition of antibodies, and cancer metastasis. Chemical synthesis provides the flexibility and, in addition, allows the preparation to be operated at large scale.
We previously developed an efficient method to prepare Gal-β1,3/4-GlcNAc disaccharides installed with orthogonal protecting groups. In order to prepare Gal-β1,3/4-GlcNAc-containing saccharides of longer chains with high total yields, we propose to utilize a disaccharide donor as a module for fast assembly. The primary concern is to study the reactivity of suitable glycosyl donors. Following the procedure developed by Prof. Wong and coworkers allowed us to obtain the relative reactivity values (RRVs) of various Gal and GlcNAc donors. The result led us to accomplish the one-pot synthesis of a LacNAc-containing tetrasaccharide. Furthermore, we would like to examine the Gal-β1,4-GlcNAc disaccharides’ RRVs. The study not only helps us to understand how incorporation of an addition sugar modulates the donor reactivity, but also makes it possible to synthesize long chain glycans with modular assembly.

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[5] Varki, A.; Cummings, R.; Esko, J.; Freeze, H.; Hart, G.; Marth, J. Essentials of Glycobioogy, 2nd ed.; CSHL, Cold Spring Harbor: New York, 1999; p 211-232.

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