均相硫酸软骨素寡糖的酶法合成。
Enzymatic Synthesis of Homogeneous Chondroitin Sulfate Oligosaccharides.
机构信息
Division of Chemical Biology and Medicinal Chemistry, Eshelman School of Pharmacy, University of North Carolina, Chapel Hill, NC, USA.
出版信息
Angew Chem Int Ed Engl. 2017 Sep 18;56(39):11784-11787. doi: 10.1002/anie.201705638. Epub 2017 Aug 17.
Abstract
Chondroitin sulfate (CS) is a sulfated polysaccharide that plays essential physiological roles. Here, we report an enzyme-based method for the synthesis of a library of 15 different CS oligosaccharides. This library covers 4-O-sulfated and 6-O-sulfated oligosaccharides ranging from trisaccharides to nonasaccharides. We also describe the synthesis of unnatural 6-O-sulfated CS pentasaccharides containing either a 6-O-sulfo-2-azidogalactosamine or a 6-O-sulfogalactosamine residue. The availability of structurally defined CS oligosaccharides offers a novel approach to investigate the biological functions of CS.
摘要
硫酸软骨素（CS）是一种具有重要生理作用的硫酸化多糖。在这里，我们报告了一种基于酶的方法，用于合成 15 种不同 CS 寡糖的文库。该文库涵盖了从三糖到九糖的 4-O-硫酸化和 6-O-硫酸化寡糖。我们还描述了含有 6-O-磺基-2-叠氮半乳糖胺或 6-O-磺基半乳糖胺残基的非天然 6-O-硫酸化 CS 五糖的合成。结构定义明确的 CS 寡糖的可用性为研究 CS 的生物学功能提供了一种新方法。
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2
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3
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Org Biomol Chem. 2017 Feb 1;15(5):1222-1227. doi: 10.1039/c6ob02603f.
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7
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Cell Microbiol. 2016 Jan;18(1):97-110. doi: 10.1111/cmi.12487. Epub 2015 Aug 31.
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