小柯机器人

科学家实现稀有糖异构体合成
2020-01-19 18:50

美国麻省理工学院Alison E. Wendlandt研究组近日取得一项新成果,他们通过位点选择性差向异构合成了稀有的糖异构体。该研究于2020年1月15日在线发表于国际一流学术期刊《自然》。

研究人员报道了通过位点选择性差向异构化反应直接从生物质碳水化合物制备稀有糖异构体。机理研究表明,这些反应是在动力学控制下进行的,即通过两个不同的催化剂介导的氢原子提取和氢原子供体的顺序步骤进行的。这种合成策略为此类有价值天然化合物提供了简洁且可能广泛的途径。

据悉,聚糖具有多种生理功能,从能量存储和结构完整性到细胞信号传导和细胞内过程的调节。尽管源自生物质的碳水化合物(例如(D)-葡萄糖、(D)-木糖和(D)-半乳糖)能够以商业规模提取,并用作可再生的化学原料和基石,但仍有数百种单糖通常无法从其天然来源中分离出来,而必须通过多步化学或酶促合成方法制备。这些“稀有”糖在具有生物活性的天然产物和药物中具有显著特征,包括许多FDA批准的抗病毒、抗菌、抗癌和强心药。

附:英文原文

Title: Synthesis of rare sugar isomers through site-selective epimerization

Author: Yong Wang, Hayden M. Carder, Alison E. Wendlandt

Issue&Volume: 2020-01-15

Abstract: Glycans have diverse physiological functions, ranging from energy storage and structural integrity to cell signalling and the regulation of intracellular processes1. Although biomass-derived carbohydrates (such as (D)-glucose, (D)-xylose and (D)-galactose) are extracted on commercial scales, and serve as renewable chemical feedstocks and building blocks2,3, there are many hundreds of distinct monosaccharides that typically cannot be isolated from their natural sources and must instead be prepared through multistep chemical or enzymatic syntheses4,5. These ‘rare’ sugars feature prominently in bioactive natural products and pharmaceuticals, including many FDA-approved antiviral, antibacterial, anti-cancer and cardiac drugs6,7. Here we report the preparation of rare sugar isomers directly from biomass carbohydrates through site-selective epimerization reactions. Mechanistic studies establish that these reactions proceed under kinetic control, through sequential steps of hydrogen atom abstraction and hydrogen atom donation mediated by two distinct catalysts. This synthetic strategy provides concise and potentially extensive access to this valuable class of natural compounds.

DOI: 10.1038/s41586-020-1937-1

Source: https://www.nature.com/articles/s41586-020-1937-1

Nature:《自然》,创刊于1869年。隶属于施普林格·自然出版集团,最新IF:43.07
官方网址:http://www.nature.com/
投稿链接:http://www.nature.com/authors/submit_manuscript.html


本期文章:《自然》:Online/在线发表

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