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Recent advances in the synthesis of extensive libraries of heparan sulfate oligosaccharides for structure-activity relationship studies.近年来,在肝素硫酸寡糖的广泛文库合成方面取得了进展,可用于结构-活性关系研究。
Curr Opin Chem Biol. 2024 Jun;80:102455. doi: 10.1016/j.cbpa.2024.102455. Epub 2024 Apr 17.
2
Using structurally defined oligosaccharides to understand the interactions between proteins and heparan sulfate.使用结构定义的寡糖来理解蛋白质和肝素硫酸之间的相互作用。
Curr Opin Struct Biol. 2018 Jun;50:155-161. doi: 10.1016/j.sbi.2018.04.003. Epub 2018 Apr 21.
3
Efficient platform for synthesizing comprehensive heparan sulfate oligosaccharide libraries for decoding glycosaminoglycan-protein interactions.高效平台用于合成全面的肝素硫酸寡糖文库,以解码糖胺聚糖-蛋白相互作用。
Nat Chem. 2023 Aug;15(8):1108-1117. doi: 10.1038/s41557-023-01248-4. Epub 2023 Jun 22.
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Continuous-Flow Accelerated Sulfation of Heparan Sulfate Intermediates.连续流加速硫酸肝素中间产物的磺化作用。
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Expedient Synthesis of Core Disaccharide Building Blocks from Natural Polysaccharides for Heparan Sulfate Oligosaccharide Assembly.从天然多糖出发快速合成核心二糖砌块用于硫酸乙酰肝素寡糖的组装。
Angew Chem Int Ed Engl. 2019 Dec 16;58(51):18577-18583. doi: 10.1002/anie.201908805. Epub 2019 Nov 6.
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Synthesis of a targeted library of heparan sulfate hexa- to dodecasaccharides as inhibitors of β-secretase: potential therapeutics for Alzheimer's disease.肝素硫酸六糖至十二糖靶向文库的合成作为β-分泌酶抑制剂:治疗阿尔茨海默病的潜在疗法。
Chemistry. 2013 May 17;19(21):6817-23. doi: 10.1002/chem.201204519. Epub 2013 Apr 3.
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Synthetic heparan sulfate oligosaccharides inhibit endothelial cell functions essential for angiogenesis.合成硫酸乙酰肝素寡糖抑制血管生成所必需的内皮细胞功能。
PLoS One. 2010 Jul 21;5(7):e11644. doi: 10.1371/journal.pone.0011644.
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Synthesis of a Systematic 64-Membered Heparan Sulfate Tetrasaccharide Library.合成一个系统性的 64 元肝素硫酸四糖文库。
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Production of size-defined heparosan, heparan sulfate, and heparin oligosaccharides by enzymatic depolymerization.通过酶促解聚生产尺寸确定的乙酰肝素、硫酸乙酰肝素和肝素寡糖。
Methods Mol Biol. 2015;1229:21-9. doi: 10.1007/978-1-4939-1714-3_3.

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Chemical synthesis of glycan motifs from the antitumor agent PI-88 through an orthogonal one-pot glycosylation strategy.通过正交一锅法糖基化策略从抗肿瘤药物PI-88化学合成聚糖基序。
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Unravelling structure-function interactions between fluorinated heparan sulfate mimetics and signaling proteins.解析氟化硫酸乙酰肝素模拟物与信号蛋白之间的结构-功能相互作用。
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Investigation into the binding domains of platelet factor 4 unlocks new avenues for the design and synthesis of selective sulfated pseudo-tetrasaccharide aminoglycoside ligands.对血小板因子4结合域的研究为选择性硫酸化假四糖氨基糖苷配体的设计与合成开辟了新途径。
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本文引用的文献

1
Efficient platform for synthesizing comprehensive heparan sulfate oligosaccharide libraries for decoding glycosaminoglycan-protein interactions.高效平台用于合成全面的肝素硫酸寡糖文库,以解码糖胺聚糖-蛋白相互作用。
Nat Chem. 2023 Aug;15(8):1108-1117. doi: 10.1038/s41557-023-01248-4. Epub 2023 Jun 22.
2
Automated Solid Phase Assisted Synthesis of a Heparan Sulfate Disaccharide Library.硫酸乙酰肝素二糖文库的自动化固相辅助合成
Org Chem Front. 2022 Jun 7;9(11):2910-2920. doi: 10.1039/d2qo00439a. Epub 2022 Apr 19.
3
Synthesis of a Systematic 64-Membered Heparan Sulfate Tetrasaccharide Library.合成一个系统性的 64 元肝素硫酸四糖文库。
Angew Chem Int Ed Engl. 2023 Jan 2;62(1):e202211985. doi: 10.1002/anie.202211985. Epub 2022 Dec 1.
4
Chemoenzymatic Synthesis of Heparan Sulfate Oligosaccharides having a Domain Structure.肝素硫酸寡糖的化学酶法合成具有结构域。
Angew Chem Int Ed Engl. 2022 Nov 21;61(47):e202211112. doi: 10.1002/anie.202211112. Epub 2022 Oct 19.
5
On resin synthesis of sulfated oligosaccharides.关于硫酸化寡糖的树脂合成
Chem Sci. 2022 Jan 31;13(7):2115-2120. doi: 10.1039/d1sc06063e. eCollection 2022 Feb 16.
6
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.
7
Synthesis of 3--Sulfated Heparan Sulfate Oligosaccharides Using 3--Sulfotransferase Isoform 4.使用 3--磺基转移酶同工酶 4 合成 3--硫酸乙酰肝素寡糖。
ACS Chem Biol. 2021 Oct 15;16(10):2026-2035. doi: 10.1021/acschembio.1c00474. Epub 2021 Aug 5.
8
Heparan Sulfate Proteoglycans as Attachment Factor for SARS-CoV-2.硫酸乙酰肝素蛋白聚糖作为新冠病毒的附着因子
ACS Cent Sci. 2021 Jun 23;7(6):1009-1018. doi: 10.1021/acscentsci.1c00010. Epub 2021 Jun 2.
9
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.
10
Heparin-Induced Thrombocytopenia: A Focus on Thrombosis.肝素诱导的血小板减少症:关注血栓形成。
Arterioscler Thromb Vasc Biol. 2021 Jan;41(1):141-152. doi: 10.1161/ATVBAHA.120.315445. Epub 2020 Dec 3.

近年来,在肝素硫酸寡糖的广泛文库合成方面取得了进展,可用于结构-活性关系研究。

Recent advances in the synthesis of extensive libraries of heparan sulfate oligosaccharides for structure-activity relationship studies.

机构信息

Department of Chemistry, Michigan State University, 578 S. Shaw Lane, East Lansing, MI 48824, USA; Chemistry Department, Faculty of Science, Benha University, Benha, Qaliobiya 13518, Egypt.

Department of Chemistry, Michigan State University, 578 S. Shaw Lane, East Lansing, MI 48824, USA.

出版信息

Curr Opin Chem Biol. 2024 Jun;80:102455. doi: 10.1016/j.cbpa.2024.102455. Epub 2024 Apr 17.

DOI:10.1016/j.cbpa.2024.102455
PMID:38636446
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11164629/
Abstract

Heparan sulfate (HS) is a linear, sulfated and highly negatively-charged polysaccharide that plays important roles in many biological events. As a member of the glycosaminoglycan (GAG) family, HS is commonly found on mammalian cell surfaces and within the extracellular matrix. The structural complexities of natural HS polysaccharides have hampered the comprehension of their biological functions and structure-activity relationships (SARs). Although the sulfation patterns and backbone structures of HS can be major determinants of their biological activities, obtaining significant amounts of pure HS from natural sources for comprehensive SAR studies is challenging. Chemical and enzyme-based synthesis can aid in the production of structurally well-defined HS oligosaccharides. In this review, we discuss recent innovations enabling the syntheses of large libraries of HS and how these libraries can provide insights into the structural preferences of various HS binding proteins.

摘要

硫酸乙酰肝素(HS)是一种线性、硫酸化且带高度负电荷的多糖,在许多生物事件中发挥着重要作用。作为糖胺聚糖(GAG)家族的一员,HS 通常存在于哺乳动物细胞表面和细胞外基质中。天然 HS 多糖的结构复杂性阻碍了对其生物功能和结构-活性关系(SAR)的理解。尽管 HS 的硫酸化模式和主链结构是其生物活性的主要决定因素,但从天然来源获得大量纯 HS 以进行全面的 SAR 研究具有挑战性。化学和酶法合成有助于生产结构明确的 HS 寡糖。在这篇综述中,我们讨论了最近的创新,这些创新使大规模 HS 文库的合成成为可能,并探讨了这些文库如何为各种 HS 结合蛋白的结构偏好提供见解。