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Δ-4,5 不饱和硫酸乙酰肝素寡糖的化学合成及其用于生物标志物的发现。

Chemical Synthesis of Δ-4,5 Unsaturated Heparan Sulfate Oligosaccharides for Biomarker Discovery.

机构信息

Complex Carbohydrate Research Center, University of Georgia, 315 Riverbend Road, Athens, Georgia 30602, United States.

Department of Chemistry, University of Georgia, Athens, Georgia 30602, United States.

出版信息

Org Lett. 2024 Mar 29;26(12):2462-2466. doi: 10.1021/acs.orglett.4c00596. Epub 2024 Mar 18.

DOI:10.1021/acs.orglett.4c00596
PMID:38498917
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10985652/
Abstract

A methodology is described that can provide heparan sulfate oligosaccharides having a Δ4,5-double bond, which are needed as analytical standards and biomarkers for mucopolysaccharidoses. It is based on chemical oligosaccharide synthesis followed by modification of the C-4 hydroxyl of the terminal uronic acid moiety as methanesulfonate. This leaving group is stable under conditions used to remove temporary protecting groups, -sulfation, and hydrogenolysis. Treatment with NaOH results in elimination of the methanesulfonate and formation of a Δ4,5-double bond.

摘要

本文描述了一种方法，可提供具有 Δ4,5-双键的肝素硫酸寡糖，这些寡糖是分析标准品和黏多糖贮积症生物标志物所必需的。它基于化学寡糖合成，然后将末端糖醛酸残基的 C-4 羟基修饰为甲磺酸酯。该离去基团在用于去除临时保护基团、-磺酸化和氢解的条件下稳定。用 NaOH 处理会导致甲磺酸酯消除并形成 Δ4,5-双键。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9dc5/10985652/45e4daafb4e8/ol4c00596_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9dc5/10985652/0a33692da59a/ol4c00596_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9dc5/10985652/34c1d62c630a/ol4c00596_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9dc5/10985652/b0a0ce39d90f/ol4c00596_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9dc5/10985652/45e4daafb4e8/ol4c00596_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9dc5/10985652/0a33692da59a/ol4c00596_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9dc5/10985652/34c1d62c630a/ol4c00596_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9dc5/10985652/b0a0ce39d90f/ol4c00596_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9dc5/10985652/45e4daafb4e8/ol4c00596_0004.jpg

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本文引用的文献

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Angew Chem Int Ed Engl. 2023 Oct 9;62(41):e202309838. doi: 10.1002/anie.202309838. Epub 2023 Sep 6.
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Glycosaminoglycans: What Remains To Be Deciphered?糖胺聚糖：还有哪些有待破解？
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Dissecting structure-function of 3-O-sulfated heparin and engineered heparan sulfates.剖析3-O-硫酸化肝素和工程化硫酸乙酰肝素的结构与功能
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Developments in the Chemical Synthesis of Heparin and Heparan Sulfate.肝素和硫酸乙酰肝素的化学合成进展。
Chem Rec. 2021 Nov;21(11):3238-3255. doi: 10.1002/tcr.202100173. Epub 2021 Sep 15.
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Discovery of rare sulfated -unsubstituted glucosamine based heparan sulfate analogs selectively activating chemokines.发现基于罕见硫酸化未取代葡糖胺的硫酸乙酰肝素类似物可选择性激活趋化因子。
Chem Sci. 2021 Jan 28;12(10):3674-3681. doi: 10.1039/d0sc05862a. eCollection 2021 Mar 14.
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The 3--sulfation of heparan sulfate modulates protein binding and lyase degradation.硫酸乙酰肝素的 3-硫酸化调节蛋白结合和裂解酶的降解。
Proc Natl Acad Sci U S A. 2021 Jan 19;118(3). doi: 10.1073/pnas.2012935118.
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Modulating Heparanase Activity: Tuning Sulfation Pattern and Glycosidic Linkage of Oligosaccharides.调节肝素酶活性：调控寡糖的硫酸化模式和糖苷键连接。
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Shotgun ion mobility mass spectrometry sequencing of heparan sulfate saccharides.肝素糖胺聚糖的 shotgun 离子迁移质谱测序。
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