从硫酸软骨素A半合成硫酸软骨素E。
Semi-synthesis of chondroitin sulfate-E from chondroitin sulfate-A.
作者信息
Cai Chao, Solakyildirim Kemal, Yang Bo, Beaudet Julie M, Weyer Amanda, Linhardt Robert J, Zhang Fuming
机构信息
Department of Chemistry and Chemical Biology, Center for Biotechnology and Interdisciplinary Studies, Rensselaer Polytechnic Institute, Troy, New York 12180, USA.
出版信息
Carbohydr Polym. 2012 Jan 4;87(1):822-829. doi: 10.1016/j.carbpol.2011.08.075.
Abstract
Chondroitin sulfate-E (chondroitin-4, 6-disulfate) was prepared from chondroitin sulfate-A (chondroitin-4 - sulfate) by regioselective sulfonation, performed using trimethylamine sulfur trioxide in formamide under argon. The structure of semi-synthetic chondroitin sulfate-E was analyzed by PAGE, (1)H NMR, (13)C NMR, 2D NMR and disaccharide analysis and compared with natural chondroitin sulfate-E. Both semi-synthetic and natural chondroitin sulfate-E were each biotinylated and immobilized on BIAcore SA biochips and their interactions with fibroblast growth factors displayed very similar binding kinetics and binding affinities. The current semi-synthesis offers an economical approach for the preparation of the rare chondroitin sulfate-E from the readily available chondroitin sulfate-A.
摘要
硫酸软骨素 - E（软骨素 - 4,6 - 二硫酸酯）由硫酸软骨素 - A（软骨素 - 4 - 硫酸酯）通过区域选择性磺化制备，该磺化反应在氩气氛围下于甲酰胺中使用三甲胺三氧化硫进行。通过聚丙烯酰胺凝胶电泳（PAGE）、氢核磁共振（¹H NMR）、碳核磁共振（¹³C NMR）、二维核磁共振（2D NMR）和二糖分析对半合成硫酸软骨素 - E的结构进行了分析，并与天然硫酸软骨素 - E进行了比较。将半合成和天然硫酸软骨素 - E分别进行生物素化并固定在BIAcore SA生物芯片上，它们与成纤维细胞生长因子的相互作用表现出非常相似的结合动力学和结合亲和力。当前的半合成方法为从易于获得的硫酸软骨素 - A制备稀有的硫酸软骨素 - E提供了一种经济的途径。
相似文献
1
Semi-synthesis of chondroitin sulfate-E from chondroitin sulfate-A.从硫酸软骨素A半合成硫酸软骨素E。
Carbohydr Polym. 2012 Jan 4;87(1):822-829. doi: 10.1016/j.carbpol.2011.08.075.
2
Conformational changes and anticoagulant activity of chondroitin sulfate following its O-sulfonation.硫酸软骨素O-磺化后的构象变化及抗凝血活性
Carbohydr Res. 1998 Jan;306(1-2):35-43. doi: 10.1016/s0008-6215(97)10060-x.
3
Structural determination of five novel tetrasaccharides containing 3-O-sulfated D-glucuronic acid and two rare oligosaccharides containing a beta-D-glucose branch isolated from squid cartilage chondroitin sulfate E.从鱿鱼软骨硫酸软骨素E中分离出的五种含3-O-硫酸化D-葡萄糖醛酸的新型四糖和两种含β-D-葡萄糖分支的稀有寡糖的结构测定
Biochemistry. 2004 Aug 31;43(34):11063-74. doi: 10.1021/bi049622d.
4
Semi-synthesis of unusual chondroitin sulfate polysaccharides containing GlcA(3-O-sulfate) or GlcA(2,3-di-O-sulfate) units.含 GlcA(3-O- 硫酸盐)或 GlcA(2,3-二-O- 硫酸盐)单元的罕见硫酸软骨素多糖的半合成。
Chemistry. 2012 Feb 13;18(7):2123-30. doi: 10.1002/chem.201102458. Epub 2012 Jan 9.
5
Syntheses of chondroitin sulfate tetrasaccharide structures containing 4,6-disulfate patterns and analysis of their interaction with glycosaminoglycan-binding protein.含有4,6 - 二硫酸模式的硫酸软骨素四糖结构的合成及其与糖胺聚糖结合蛋白相互作用的分析
Bioorg Med Chem Lett. 2015 Apr 1;25(7):1552-5. doi: 10.1016/j.bmcl.2015.02.011. Epub 2015 Feb 16.
6
Glycosaminoglycans of the porcine central nervous system.猪中枢神经系统的糖胺聚糖。
Biochemistry. 2010 Nov 16;49(45):9839-47. doi: 10.1021/bi101305b. Epub 2010 Oct 26.
7
Deciphering Structural Determinants in Chondroitin Sulfate Binding to FGF-2: Paving the Way to Enhanced Predictability of their Biological Functions.解析硫酸软骨素与FGF-2结合的结构决定因素：为增强其生物学功能的可预测性铺平道路。
Polymers (Basel). 2021 Jan 19;13(2):313. doi: 10.3390/polym13020313.
8
9
Structural and functional characterization of oversulfated chondroitin sulfate/dermatan sulfate hybrid chains from the notochord of hagfish. Neuritogenic and binding activities for growth factors and neurotrophic factors.盲鳗脊索中过度硫酸化硫酸软骨素/硫酸皮肤素杂合链的结构与功能表征。对生长因子和神经营养因子的促神经突生长及结合活性。
J Biol Chem. 2004 Dec 3;279(49):50799-809. doi: 10.1074/jbc.M404746200. Epub 2004 Sep 22.
10
Novel tetrasaccharides isolated from squid cartilage chondroitin sulfate E contain unusual sulfated disaccharide units GlcA(3-O-sulfate)beta1-3GalNAc(6-O-sulfate) or GlcA(3-O-sulfate)beta1-3GalNAc.从鱿鱼软骨硫酸软骨素E中分离出的新型四糖含有不寻常的硫酸化二糖单元GlcA(3-O-硫酸酯)β1-3GalNAc(6-O-硫酸酯)或GlcA(3-O-硫酸酯)β1-3GalNAc。
J Biol Chem. 1997 Aug 8;272(32):19656-65. doi: 10.1074/jbc.272.32.19656.
引用本文的文献
1
Biosynthesis of animal-free recombinant chondroitin sulfate E using a functional chondroitin sulfotransferase in E. coli.利用大肠杆菌中的功能性硫酸软骨素转移酶合成无动物源重组硫酸软骨素 E。
Appl Microbiol Biotechnol. 2024 Aug 15;108(1):440. doi: 10.1007/s00253-024-13275-3.
2
Neuritogenic glycosaminoglycan hydrogels promote functional recovery after severe traumatic brain injury.神经发生性糖胺聚糖水凝胶促进严重外伤性脑损伤后的功能恢复。
J Neural Eng. 2024 Jun 27;21(3):036058. doi: 10.1088/1741-2552/ad5108.
3
Structural Characterization and Glycosaminoglycan Impurities Analysis of Chondroitin Sulfate from Chinese Sturgeon.中华鲟硫酸软骨素的结构表征及糖胺聚糖杂质分析
Polymers (Basel). 2022 Dec 5;14(23):5311. doi: 10.3390/polym14235311.
4
Pleiotrophin interacts with glycosaminoglycans in a highly flexible and adaptable manner.pleiotrophin 以高度灵活和适应性的方式与糖胺聚糖相互作用。
FEBS Lett. 2021 Apr;595(7):925-941. doi: 10.1002/1873-3468.14052. Epub 2021 Feb 12.
5
Research and Application of Chondroitin Sulfate/Dermatan Sulfate-Degrading Enzymes.硫酸软骨素/硫酸皮肤素降解酶的研究与应用
Front Cell Dev Biol. 2020 Dec 3;8:560442. doi: 10.3389/fcell.2020.560442. eCollection 2020.
6
Role of Chondroitin Sulfation Following Spinal Cord Injury.脊髓损伤后硫酸软骨素硫酸化的作用。
Front Cell Neurosci. 2020 Aug 5;14:208. doi: 10.3389/fncel.2020.00208. eCollection 2020.
7
A Study for the Access to a Semi-synthetic Regioisomer of Natural Fucosylated Chondroitin Sulfate with Fucosyl Branches on -acetyl-Galactosamine Units.一种获取天然岩藻糖基硫酸软骨素半合成区域异构体的研究，该异构体在 N-乙酰半乳糖胺单元上具有岩藻糖支链。
Mar Drugs. 2019 Nov 21;17(12):655. doi: 10.3390/md17120655.
8
Surfen-mediated blockade of extratumoral chondroitin sulfate glycosaminoglycans inhibits glioblastoma invasion. Surf 介导的细胞外软骨素硫酸糖胺聚糖阻断抑制脑胶质母细胞瘤侵袭。
FASEB J. 2019 Nov;33(11):11973-11992. doi: 10.1096/fj.201802610RR. Epub 2019 Aug 9.
9
Glioma Cell Invasion is Significantly Enhanced in Composite Hydrogel Matrices Composed of Chondroitin 4- and 4,6-Sulfated Glycosaminoglycans.在由4-硫酸软骨素和4,6-硫酸化糖胺聚糖组成的复合水凝胶基质中，胶质瘤细胞的侵袭显著增强。
J Mater Chem B. 2016;4(36):6052-6064. doi: 10.1039/C6TB01083K. Epub 2016 Aug 26.
10
Structural studies reveal an important role for the pleiotrophin C-terminus in mediating interactions with chondroitin sulfate.结构研究揭示了多效生长因子C末端在介导与硫酸软骨素相互作用中的重要作用。
FEBS J. 2016 Apr;283(8):1488-503. doi: 10.1111/febs.13686. Epub 2016 Mar 6.
本文引用的文献
1
Glycosaminoglycans of the porcine central nervous system.猪中枢神经系统的糖胺聚糖。
Biochemistry. 2010 Nov 16;49(45):9839-47. doi: 10.1021/bi101305b. Epub 2010 Oct 26.
2
Ultraperformance liquid chromatography with electrospray ionization ion trap mass spectrometry for chondroitin disaccharide analysis.采用电喷雾电离离子阱质谱的超高效液相色谱法进行软骨素二糖分析。
Anal Biochem. 2010 Feb 1;397(1):24-8. doi: 10.1016/j.ab.2009.09.031. Epub 2009 Sep 19.
3
Involvement of chondroitin sulfate E in the liver tumor focal formation of murine osteosarcoma cells.硫酸软骨素E参与小鼠骨肉瘤细胞肝肿瘤灶形成
Glycobiology. 2009 Jul;19(7):735-42. doi: 10.1093/glycob/cwp041. Epub 2009 Mar 17.
4
Chondroitin sulfate E fragments enhance CD44 cleavage and CD44-dependent motility in tumor cells.硫酸软骨素E片段增强肿瘤细胞中CD44的裂解及CD44依赖性运动能力。
Cancer Res. 2008 Sep 1;68(17):7191-9. doi: 10.1158/0008-5472.CAN-07-6198.
5
Oversulfated chondroitin sulfate-E binds to BMP-4 and enhances osteoblast differentiation.过硫酸化硫酸软骨素-E与骨形态发生蛋白-4结合并增强成骨细胞分化。
J Cell Physiol. 2008 Dec;217(3):769-77. doi: 10.1002/jcp.21557.
6
A highly sulfated chondroitin sulfate preparation, CS-E, prevents excitatory amino acid-induced neuronal cell death.一种高度硫酸化的硫酸软骨素制剂，CS-E，可预防兴奋性氨基酸诱导的神经元细胞死亡。
J Neurochem. 2008 Mar;104(6):1565-76. doi: 10.1111/j.1471-4159.2007.05107.x. Epub 2007 Nov 7.
7
Chondroitin/dermatan sulfate in the central nervous system.中枢神经系统中的硫酸软骨素/硫酸皮肤素
Curr Opin Struct Biol. 2007 Oct;17(5):536-45. doi: 10.1016/j.sbi.2007.08.015. Epub 2007 Oct 24.
8
Protease-proteoglycan complexes of mouse and human mast cells and importance of their beta-tryptase-heparin complexes in inflammation and innate immunity.小鼠和人类肥大细胞的蛋白酶-蛋白聚糖复合物及其β-组织蛋白酶-肝素复合物在炎症和固有免疫中的重要性。
Immunol Rev. 2007 Jun;217:155-67. doi: 10.1111/j.1600-065X.2007.00525.x.
9
Novel sulfated octa- and decasaccharides from squid cartilage chondroitin sulfate E: sequencing and application for determination of the epitope structure of the monoclonal antibody MO-225.来自鱿鱼软骨硫酸软骨素E的新型硫酸化八糖和十糖：测序及用于单克隆抗体MO-225表位结构测定
Biochemistry. 2007 Mar 6;46(9):2453-65. doi: 10.1021/bi602374m. Epub 2007 Feb 7.
10
Role of the sulfation pattern of chondroitin sulfate in its biological activities and in the binding of growth factors.硫酸软骨素的硫酸化模式在其生物学活性及生长因子结合中的作用。
Adv Pharmacol. 2006;53:253-79. doi: 10.1016/S1054-3589(05)53012-6.
Zotero 插件