无保护糖基化反应研究进展

doi:10.6023/cjoc202211024

摘要/Abstract

糖类在很多生命活动中发挥着重要的作用, 例如细胞壁组成、能量储存以及生物识别等. 发展高区域选择性和立体选择性的糖基化反应是目前糖化学研究的中心问题. 传统的化学糖基化方法往往需要依靠正交的保护基化学来调控糖基化反应的选择性. 近年来一些无保护糖基化的策略被开发出来, 可以在更简单、更温和的条件下实现寡糖及其缀合物的选择性合成. 对近期发展的无保护糖基化策略进行了综述, 并对无保护糖基化反应的未来发展前景进行展望.

关键词: 化学糖基化反应, 无保护, 直接端基活化, 糖化学

Carbohydrates play a key role in many life activities, such as cell wall composition, energy storage and biological recognition. Development of highly regio- and stereo-selective glycosylation reactions is a central topic of current carbohydrate chemistry. The traditional glycosylation protocol usually requires the orthogonal protecting chemistry to obtain the selectivity of glycosylation reactions. Recent progress in protecting-group free strategies can provide a simple and mild approach to the chemo-selective construction of glycosidic bonds in oligosaccharides or glycoconjugates in aqueous conditions. The latest advances in protection-free chemical glycosylations are summarized, including the direct anomeric activation strategy developed by our group.

Key words: chemical glycosylation, protection-free, direct anomeric activation, carbohydrate chemistry

引用此文

李格非, 荆杰, 罗振扬, 默娟, 熊德彩, 叶新山. 无保护糖基化反应研究进展[J]. 有机化学, 2023, 43(6): 1991-2001.

Gefei Li, Jie Jing, Zhenyang Luo, Juan Mo, Decai Xiong, Xinshan Ye. Recent Advances in Protection-Free Glycosylations[J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 1991-2001.

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图/表 11

图式1. 保护/无保护糖基化反应的一般过程

Scheme 1. General glycosylation process with or without protecting chemistry

图1. 糖基化反应过程: (A)基于氢键作用的酶促糖基化; (B)基于金属离子键合的化学糖基化

Figure 1. Glycosylation mechanism: (A) enzymatic process based on H-bonding interaction; (B) chemical process relied on metal ion binding

图式2. 钙离子诱导的基于氟代糖供体的无保护水相糖基化反应

Scheme 2. Calcium ion mediated aqueous protecting-group free glycosylation using fluoroglycoside donors

图式3. 硼酸介导的选择性糖基化反应

Scheme 3. Regio- and stereo-selective glycosylation using a boronic acid catalyst

图式4. 水溶液中糖分子还原末端直接活化策略用于制备酶促糖基化反应的糖供体

Scheme 4. Direct anomeric activation strategy for the synthesis of glycosyl donors used in the chemo-enzymatic glycosylation

图式5. 用于无保护糖基化的DBT-糖基供体

Scheme 5. Development of DBT-glycosyl donors used for protecting-group free glycosylation

图式6. 水溶液中的两步缩合过程

Scheme 6. Concept of dehydrative process in water

图式7. 正田试剂在糖链还原末端直接活化方面的应用

Scheme 7. Applications of Shoda’s reagent in direct anomeric activation

图式8. Fischer糖基化反应的研究进展

Scheme 8. Current progress in Fischer glycosylation

图式9. 其他类型的无保护糖基化反应

Scheme 9. Other protecting-group free glycosylation reactions

图2. 基于无保护-水相糖化学循环理念的生物活性糖分子制备

Figure 2. Production of bioactive carbohydrates based on the concept of “Glyco-chemistry Cycle System”

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