2-氨基乙基葡糖胺磺基形式的固相合成
Solid-Phase Synthesis of 2-Aminoethyl Glucosamine Sulfoforms.
作者信息
Liu Runhui, Wei Alexander
机构信息
Department of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, IN 47907-2084.
出版信息
J Carbohydr Chem. 2012 Jan 1;31(4-6):384-419. doi: 10.1080/07328303.2012.658274. Epub 2012 Jul 2.
Abstract
Mono- and disaccharides of sulfonated glucosamines (GlcN sulfoforms) conjugated to 2-aminoethyl linkers were generated by solid-phase synthesis. Orthogonally protected intermediates were tethered onto tritylated polystyrene resin beads, subjected to a modular sequence of deprotection and sulfonation steps, then cleaved from solid support without degradation of N- or O-sulfate esters using solvolytic conditions, and finally purified by reverse-phase HPLC to afford the title compounds.
摘要
通过固相合成法生成了与2-氨基乙基连接体共轭的磺化葡糖胺（葡糖胺磺化形式）的单糖和二糖。将正交保护的中间体连接到三苯甲基化的聚苯乙烯树脂珠上，进行脱保护和磺化步骤的模块化序列，然后在不使用溶剂解条件降解N-或O-硫酸酯的情况下从固相载体上裂解下来，最后通过反相高效液相色谱法纯化，得到标题化合物。
相似文献
1
Solid-Phase Synthesis of 2-Aminoethyl Glucosamine Sulfoforms.2-氨基乙基葡糖胺磺基形式的固相合成
J Carbohydr Chem. 2012 Jan 1;31(4-6):384-419. doi: 10.1080/07328303.2012.658274. Epub 2012 Jul 2.
2
Solid-phase synthesis of alpha-glucosamine sulfoforms with fragmentation analysis by tandem mass spectrometry.通过串联质谱进行碎片分析的α-氨基葡萄糖磺基形式的固相合成。
J Org Chem. 2008 Aug 15;73(16):6059-72. doi: 10.1021/jo800713m. Epub 2008 Jul 9.
3
Sulfoform generation from an orthogonally protected disaccharide.从正交保护的二糖生成磺酸酯。
Carbohydr Res. 2012 Jul 1;355:19-27. doi: 10.1016/j.carres.2012.04.010. Epub 2012 Apr 21.
4
Homogeneous sulfopeptides and sulfoproteins: synthetic approaches and applications to characterize the effects of tyrosine sulfation on biochemical function.均一化的磺酸肽和磺基蛋白：合成方法及其在酪氨酸磺酸化对生化功能影响的研究中的应用。
Acc Chem Res. 2015 Aug 18;48(8):2251-61. doi: 10.1021/acs.accounts.5b00255. Epub 2015 Jul 21.
5
Synthesis and characterization of sulfated Gal-β-1,3/4-GlcNAc disaccharides through consecutive protection/glycosylation steps.通过连续的保护/糖苷化步骤合成并表征硫酸化 Gal-β-1,3/4-GlcNAc 二糖。
Chem Asian J. 2013 Jul;8(7):1536-50. doi: 10.1002/asia.201201204. Epub 2013 May 2.
6
Modulation of articular chondrocyte proliferation and anionic glycoconjugate synthesis by glucosamine (GlcN), N-acetyl GlcN (GlcNAc) GlcN sulfate salt (GlcN.S) and covalent glucosamine sulfates (GlcN-SO4).氨基葡萄糖（GlcN）、N-乙酰氨基葡萄糖（GlcNAc）、氨基葡萄糖硫酸盐（GlcN.S）和共价氨基葡萄糖硫酸盐（GlcN-SO4）对关节软骨细胞增殖及阴离子糖缀合物合成的调节作用
Osteoarthritis Cartilage. 2007 Aug;15(8):946-56. doi: 10.1016/j.joca.2007.02.010. Epub 2007 Apr 2.
7
An expeditious preparation of various sulfoforms of the disaccharide beta-D-Galp-(1-->3)-D-Galp, a partial structure of the linkage region of proteoglycans, as their 4-methoxyphenyl beta-D-glycosides.一种快速制备二糖β-D-半乳糖基-(1→3)-D-半乳糖的各种磺基形式的方法，该二糖是蛋白聚糖连接区的部分结构，以其4-甲氧基苯基β-D-糖苷形式存在。
Carbohydr Res. 2004 Jan 22;339(2):349-59. doi: 10.1016/j.carres.2003.10.012.
8
Solid-phase synthesis of symmetrical 5',5'-dinucleoside mono-, di-, tri-, and tetraphosphodiesters.对称5',5'-二核苷单磷酸酯、二磷酸酯、三磷酸酯和四磷酸酯的固相合成。
Org Lett. 2007 Oct 25;9(22):4483-6. doi: 10.1021/ol7018778. Epub 2007 Oct 4.
9
Solid-phase synthesis of protected peptides using new cobalt(III) ammine linkers.
Int J Pept Protein Res. 1993 Aug;42(2):138-54. doi: 10.1111/j.1399-3011.1993.tb00490.x.
10
Acid-Stable Ester Linkers for the Solid-Phase Synthesis of Immobilized Peptides.用于固定化肽的固相合成的酸稳定酯连接剂。
Chempluschem. 2020 Jun;85(6):1297-1306. doi: 10.1002/cplu.202000246.
引用本文的文献
1
Sulfoform generation from an orthogonally protected disaccharide.从正交保护的二糖生成磺酸酯。
Carbohydr Res. 2012 Jul 1;355:19-27. doi: 10.1016/j.carres.2012.04.010. Epub 2012 Apr 21.
本文引用的文献
1
A new linker for solid-phase synthesis of heparan sulfate precursors by sequential assembly of monosaccharide building blocks.一种新的连接子，通过单糖砌块的顺序组装用于肝素硫酸酯前体的固相合成。
Chem Commun (Camb). 2011 Feb 28;47(8):2390-2. doi: 10.1039/c0cc04686h. Epub 2010 Dec 20.
2
Solid-phase synthesis of alpha-glucosamine sulfoforms with fragmentation analysis by tandem mass spectrometry.通过串联质谱进行碎片分析的α-氨基葡萄糖磺基形式的固相合成。
J Org Chem. 2008 Aug 15;73(16):6059-72. doi: 10.1021/jo800713m. Epub 2008 Jul 9.
3
Chemo-enzymatic supported synthesis of the 3-sulfated Lewis a pentasaccharide on a multimeric polyethylene glycol.在多聚乙二醇上通过化学酶法支持合成3 - 硫酸化路易斯a五糖。
Carbohydr Res. 2008 Apr 7;343(5):970-6. doi: 10.1016/j.carres.2008.01.005. Epub 2008 Jan 15.
4
Cooperativity in glycan-protein interactions.
Chem Biol. 2007 Aug;14(8):873-4. doi: 10.1016/j.chembiol.2007.08.003.
5
Profiling the sulfation specificities of glycosaminoglycan interactions with growth factors and chemotactic proteins using microarrays.使用微阵列分析糖胺聚糖与生长因子和趋化蛋白相互作用的硫酸化特异性。
Chem Biol. 2007 Feb;14(2):195-208. doi: 10.1016/j.chembiol.2006.12.009.
6
Preparation and use of microarrays containing synthetic heparin oligosaccharides for the rapid analysis of heparin-protein interactions.用于快速分析肝素-蛋白质相互作用的含合成肝素寡糖微阵列的制备与应用
Chemistry. 2006 Nov 24;12(34):8664-86. doi: 10.1002/chem.200601103.
7
Glycomics approach to structure-function relationships of glycosaminoglycans.糖组学方法研究糖胺聚糖的结构-功能关系
Annu Rev Biomed Eng. 2006;8:181-231. doi: 10.1146/annurev.bioeng.8.061505.095745.
8
Orthogonal sulfation strategy for synthetic heparan sulfate ligands.合成硫酸乙酰肝素配体的正交硫酸化策略
Org Lett. 2005 Oct 27;7(22):5095-8. doi: 10.1021/ol052130o.
9
Structural insights into biological roles of protein-glycosaminoglycan interactions.蛋白质-糖胺聚糖相互作用生物学作用的结构见解
Chem Biol. 2005 Mar;12(3):267-77. doi: 10.1016/j.chembiol.2004.11.020.
10
Fibroblast growth factors share binding sites in heparan sulphate.成纤维细胞生长因子在硫酸乙酰肝素中共享结合位点。
Biochem J. 2005 Jul 1;389(Pt 1):145-50. doi: 10.1042/BJ20042129.
Zotero 插件