生物素化肝素六糖的简便化学酶法合成
Facile chemoenzymatic synthesis of biotinylated heparosan hexasaccharide.
作者信息
Wu Baolin, Wei Na, Thon Vireak, Wei Mohui, Yu Zaikuan, Xu Yongmei, Chen Xi, Liu Jian, Wang Peng George, Li Tiehai
机构信息
Center for Diagnostics and Therapeutics, Department of Chemistry, Georgia State University, Atlanta, GA 30303, USA.
出版信息
Org Biomol Chem. 2015 May 14;13(18):5098-101. doi: 10.1039/c5ob00462d.
Abstract
A biotinylated heparosan hexasaccharide was synthesized using a one-pot multi-enzyme strategy, in situ activation and transfer of N-trifluoroacetylglucosamine (GlcNTFA) to a heparin backbone significantly improved the synthetic efficiency. The biotinylated hexasaccharide could serve as a flexible core to diversify its conversion into heparan sulfate isoforms with potential biological applications and therapeutics.
摘要
采用一锅多酶策略合成了生物素化的硫酸乙酰肝素六糖，将N-三氟乙酰葡糖胺（GlcNTFA）原位活化并转移至肝素主链显著提高了合成效率。该生物素化六糖可作为一个灵活的核心，用于多样化转化为具有潜在生物学应用和治疗用途的硫酸乙酰肝素异构体。
相似文献
1
Facile chemoenzymatic synthesis of biotinylated heparosan hexasaccharide.生物素化肝素六糖的简便化学酶法合成
Org Biomol Chem. 2015 May 14;13(18):5098-101. doi: 10.1039/c5ob00462d.
2
Metabolic engineering of non-pathogenic Escherichia coli strains for the controlled production of low molecular weight heparosan and size-specific heparosan oligosaccharides.用于控制生产低分子量肝素聚糖和特定大小肝素聚糖寡糖的非致病性大肠杆菌菌株的代谢工程。
Biochim Biophys Acta Gen Subj. 2021 Jan;1865(1):129765. doi: 10.1016/j.bbagen.2020.129765. Epub 2020 Oct 16.
3
Sugar Chips immobilized with synthetic sulfated disaccharides of heparin/heparan sulfate partial structure.固定有肝素/硫酸乙酰肝素部分结构的合成硫酸化二糖的糖芯片。
Bioorg Med Chem Lett. 2008 Apr 1;18(7):2499-504. doi: 10.1016/j.bmcl.2008.01.069. Epub 2008 Jan 19.
4
Chemoenzymatic Synthesis of Glycosaminoglycans.糖胺聚糖的酶促化学合成。
Acc Chem Res. 2020 Feb 18;53(2):335-346. doi: 10.1021/acs.accounts.9b00420. Epub 2019 Nov 12.
5
Anomeric reactivity-based one-pot synthesis of heparin-like oligosaccharides.基于异头物反应性的肝素样寡糖一锅法合成。
J Am Chem Soc. 2007 Oct 24;129(42):12795-800. doi: 10.1021/ja073098r. Epub 2007 Oct 3.
6
Chemoenzymatic design of heparan sulfate oligosaccharides.肝素硫酸寡糖的化学酶法设计。
J Biol Chem. 2010 Oct 29;285(44):34240-9. doi: 10.1074/jbc.M110.159152. Epub 2010 Aug 21.
7
Chemoenzymatic quantification for monitoring unpurified polysaccharide in rich medium.酶化学定量法用于监测富培养介质中未纯化的多糖。
Appl Microbiol Biotechnol. 2019 Sep;103(18):7635-7645. doi: 10.1007/s00253-019-10042-7. Epub 2019 Aug 1.
8
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.
9
The synthesis of biotinylated carbohydrates as probes for carbohydrate-recognizing proteins.作为碳水化合物识别蛋白探针的生物素化碳水化合物的合成。
Bioorg Med Chem. 2000 Dec;8(12):2709-18. doi: 10.1016/s0968-0896(00)00201-7.
10
Enzymatic construction of a library of even- and odd-numbered heparosan oligosaccharides and their N-sulfonated derivatives.酶法构建偶数和奇数肝素寡糖及其 N-磺化衍生物文库。
Int J Biol Macromol. 2024 Apr;264(Pt 1):130501. doi: 10.1016/j.ijbiomac.2024.130501. Epub 2024 Mar 3.
引用本文的文献
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
Glycoconjugates of Mucochloric Acid-Synthesis and Biological Activity.粘氯酸的糖缀合物——合成与生物活性
Pharmaceuticals (Basel). 2023 Mar 31;16(4):525. doi: 10.3390/ph16040525.
3
Heparan sulfate glycomimetics iterative assembly of "clickable" disaccharides.硫酸乙酰肝素糖模拟物：“可点击”二糖的迭代组装
Chem Sci. 2023 Feb 28;14(13):3514-3522. doi: 10.1039/d3sc00260h. eCollection 2023 Mar 29.
4
Engineer Heparosan Synthase 2 (PmHS2) for Size-Controlled Synthesis of Longer Heparosan Oligosaccharides.工程化改造硫酸乙酰肝素合酶2（PmHS2）以实现尺寸可控的更长硫酸乙酰肝素寡糖的合成。
ACS Catal. 2020 Jun 5;10(11):6113-6118. doi: 10.1021/acscatal.0c01231. Epub 2020 May 11.
5
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.
6
3-O sulfation of heparin leads to hepatotropism and longer circulatory half-life.肝素的 3-O 磺酸化导致肝靶向性和更长的循环半衰期。
Thromb Res. 2018 Jul;167:80-87. doi: 10.1016/j.thromres.2018.05.018. Epub 2018 May 17.
7
Chemoenzymatic synthesis of unmodified heparin oligosaccharides: cleavage of p-nitrophenyl glucuronide by alkaline and Smith degradation.未修饰肝素寡糖的化学酶法合成：通过碱法和史密斯降解法切割对硝基苯基葡糖醛酸苷
Org Biomol Chem. 2017 Feb 1;15(5):1222-1227. doi: 10.1039/c6ob02603f.
本文引用的文献
1
First Synthetic Carbohydrates with the Full Anticoagulant Properties of Heparin.具有肝素完全抗凝特性的首批合成碳水化合物。
Angew Chem Int Ed Engl. 1998 Nov 16;37(21):3009-3014. doi: 10.1002/(SICI)1521-3773(19981116)37:21<3009::AID-ANIE3009>3.0.CO;2-F.
2
Chemoenzymatic synthesis of heparan sulfate and heparin.硫酸乙酰肝素和肝素的化学酶法合成。
Nat Prod Rep. 2014 Dec;31(12):1676-85. doi: 10.1039/c4np00076e. Epub 2014 Sep 8.
3
Synthesis of the heparin-based anticoagulant drug fondaparinux.基于肝素的抗凝药物磺达肝素的合成。
Angew Chem Int Ed Engl. 2014 Sep 8;53(37):9876-9. doi: 10.1002/anie.201404154. Epub 2014 Jul 15.
4
Total synthesis of anticoagulant pentasaccharide fondaparinux.抗凝剂戊糖磺达肝癸钠的全合成。
ChemMedChem. 2014 May;9(5):1071-80. doi: 10.1002/cmdc.201400019. Epub 2014 Apr 11.
5
Synthetic oligosaccharides as active pharmaceutical ingredients: lessons learned from the full synthesis of one heparin derivative on a large scale.合成寡糖作为活性药物成分：从大规模全合成一种肝素衍生物中获得的经验教训。
Nat Prod Rep. 2014 Aug;31(8):980-9. doi: 10.1039/c4np00012a.
6
Homogeneous low-molecular-weight heparins with reversible anticoagulant activity.具有可逆抗凝活性的均一低分子量肝素。
Nat Chem Biol. 2014 Apr;10(4):248-50. doi: 10.1038/nchembio.1459. Epub 2014 Feb 23.
7
Synthesis of Fondaparinux: modular synthesis investigation for heparin synthesis.磺达肝素钠的合成：肝素合成的模块化合成研究。
Carbohydr Res. 2013 Apr 19;371:32-9. doi: 10.1016/j.carres.2013.01.003. Epub 2013 Jan 16.
8
Strategies in synthesis of heparin/heparan sulfate oligosaccharides: 2000-present.2000年至今肝素/硫酸乙酰肝素寡糖合成策略
Adv Carbohydr Chem Biochem. 2012;67:95-136. doi: 10.1016/B978-0-12-396527-1.00003-6.
9
α-Glycosylation by D-glucosamine-derived donors: synthesis of heparosan and heparin analogues that interact with mycobacterial heparin-binding hemagglutinin.D-葡萄糖胺供体的α-糖基化：肝素和肝素类似物的合成，这些物质与分枝杆菌肝素结合血凝素相互作用。
J Am Chem Soc. 2012 May 30;134(21):8988-95. doi: 10.1021/ja302640p. Epub 2012 May 15.
10
NahK/GlmU fusion enzyme: characterization and one-step enzymatic synthesis of UDP-N-acetylglucosamine.NahK/GlmU 融合酶：特性鉴定及 UDP-N-乙酰葡萄糖胺的一步酶法合成。
Biotechnol Lett. 2012 Jul;34(7):1321-6. doi: 10.1007/s10529-012-0910-y. Epub 2012 Mar 29.
Zotero 插件