思考影响1,2-半乳糖基化的结构因素：从半乳糖胺的3-半乳糖基化中获得的经验教训
Pondering the Structural Factors that Affect 1,2--Galactosylation: A Lesson Learnt from 3---Galactosylation of Galactosamine.
作者信息
Li Qingjiang, Guo Zhongwu
机构信息
Department of Chemistry, University of Florida, 214 Leigh Hall, Gainesville, Florida 32611, United States.
出版信息
J Carbohydr Chem. 2018;47(5):347-362. doi: 10.1080/07328303.2017.1406095. Epub 2017 Dec 12.
Abstract
Stereoselective formation of glycosidic bonds remains one of the most challenging topics in carbohydrate chemistry. The predominant method for stereoselective construction of 1,2--glycosidic bonds is through the neighboring group participation effect (NGPE), which proved to be less successful in synthesizing Gal(1→3)GalNAc disaccharide. The steric effect that overshadows NGPE and the impacts of substituents at the 3-- and 2--positions of donors and acceptors, respectively, on this synthesis were systematically examined to lead to some practical guidelines for choosing protecting groups towards the successful synthesis of Gal(1→3)GalNAc and similar disaccharides.
摘要
糖苷键的立体选择性形成仍然是碳水化合物化学中最具挑战性的课题之一。立体选择性构建1,2-糖苷键的主要方法是通过邻基参与效应（NGPE），事实证明该方法在合成Gal(1→3)GalNAc二糖方面不太成功。系统研究了掩盖NGPE的空间效应以及供体和受体3-位和2-位取代基对该合成的影响，从而得出一些选择保护基的实用指导原则，以成功合成Gal(1→3)GalNAc及类似二糖。
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