統計分析遠端參與效應於葡萄糖與半乳糖硫苷醣予體醣鍵結反應

Abstract

醣鍵結反應是醣化學中最重要的反應，但控制其立體選擇性和產率依然是多醣合成的主要挑戰。傳統上，合成1,2-反式醣苷鍵大多利用鄰基效應進行合成。然而尚未得出合成1,2-順式醣苷鍵的通用方法。近期發現了通過位於C-3、C-4或C-6上安裝乙醯基進行的遠程參與來控制醣鍵結反應之立體選擇性。但是，由於羰基的參與程度不明確，這種合成策略在多醣的合成中仍然不實用。根據本文研究，沿用本實驗室之預測模型，利用統計方法分析醣鍵結反應之立體選擇性，利用C-3，C-4以及C-6位置的乙醯基醣予體與不同位置羥基之醣受體分析其反應性之相關性，並且觀察是否造成遠端效應之存在。工作流程概述分為四個部分，包括準備醣予體和醣受體、檢測 RRV 和 Aka、進行醣鍵結反應和統計分析其相關性。Glycosylation is the most important reaction in glycoscience, but controlling stereoselectivity and yield remain the major challenge in the synthesis of oligosaccharides. Traditionally, constructing 1,2-trans glycosidic linkage is relied on neighboring group effect. However, a universal method for the preparation of 1,2-cis linkage is absent. Recently, remote participation by installing C-3, C-4, or C-6 acetyl group was developed to control the stereoselective glycosylation. However, this strategy is still not practical in the synthesis of oligosaccharide due to the unclear participating level of carbonyl group.According to our research, a quantitative system was established to analyze the stereoselective glycosylation using statistical approach. Herein, we study the correlation between the participating level and acetyl group at C-3, C-4 and C-6 position by using statistical approach. Overview of workflow is four parts including preparing donor and acceptor, detecting the RRV and Aka, doing glycosylation and analyzing the correlation.