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在半乳糖残基的C-3位带有O-甲基或O-磺基的Gal-β-(1→4)-GlcNac-β-(1→6)-[Gal-β-(1→3)]-GalNAc-α-OBn寡糖的合成:Gal:3-O-磺基转移酶的特异性受体。

Synthesis of Gal-beta-(1-->4)-GlcNac-beta-(1-->6)-[Gal-beta-(1-->3]-GalNAc-alpha- OBn oligosaccharides bearing O-methyl or O-sulfo groups at C-3 of the Gal residue: specific acceptors for Gal: 3-O-sulfotransferases.

作者信息

Jain R K, Piskorz C F, Chandrasekaran E V, Matta K L

机构信息

Department of Gynecologic Oncology, Roswell Park Cancer Institute, Buffalo, NY 14263, USA.

出版信息

Glycoconj J. 1998 Oct;15(10):951-9. doi: 10.1023/a:1006977607394.

DOI:10.1023/a:1006977607394
PMID:10211700
Abstract

Our recent studies have revealed the existence of two distinct Gal: 3-O-sulfotransferases capable of acting on the C-3 position of galactose in a Core 2 branched structure, e.g., Galbeta1-->4GlcNAcbeta1-->6(Galbeta1-->3)GalNacalph a1-->OBenzyl as acceptor to give 3-O-sulfoGalbeta1-->4GlcNAcbeta1-->3(Galbeta1-->3)G alNAcalpha1-->OB 20 and Galbeta1-->4GlcNAcbeta1-->6(3-O-sulfoGalbeta1-->3)G alNAcalpha1-->OB 23. We herein report the synthesis of these two compounds and also that of other modified analogs that are highly specific acceptors for the two sulfotransferases. Appropriately protected 1-thio-glycosides 7, 8, and 10 were employed as glycosyl donors for the synthesis of our target compounds.

摘要

我们最近的研究揭示了两种不同的半乳糖3 - O -磺基转移酶的存在,它们能够作用于核心2分支结构中半乳糖的C - 3位,例如,以Galβ1→4GlcNAcβ1→6(Galβ1→3)GalNAcalpha1→OBenzyl作为受体,生成3 - O - 磺基Galβ1→4GlcNAcβ1→3(Galβ1→3)GalNAcalpha1→OB 20和Galβ1→4GlcNAcβ1→6(3 - O - 磺基Galβ1→3)GalNAcalpha1→OB 23。我们在此报告这两种化合物以及其他修饰类似物的合成,这些类似物是这两种磺基转移酶的高度特异性受体。合适保护的1 - 硫代糖苷7、8和10被用作糖基供体来合成我们的目标化合物。

相似文献

1
Synthesis of Gal-beta-(1-->4)-GlcNac-beta-(1-->6)-[Gal-beta-(1-->3]-GalNAc-alpha- OBn oligosaccharides bearing O-methyl or O-sulfo groups at C-3 of the Gal residue: specific acceptors for Gal: 3-O-sulfotransferases.在半乳糖残基的C-3位带有O-甲基或O-磺基的Gal-β-(1→4)-GlcNac-β-(1→6)-[Gal-β-(1→3)]-GalNAc-α-OBn寡糖的合成:Gal:3-O-磺基转移酶的特异性受体。
Glycoconj J. 1998 Oct;15(10):951-9. doi: 10.1023/a:1006977607394.
2
The enzymatic sulfation of glycoprotein carbohydrate units: blood group T-hapten specific and two other distinct Gal:3-O-sulfotransferases as evident from specificities and kinetics and the influence of sulfate and fucose residues occurring in the carbohydrate chain on C-3 sulfation of terminal Gal.糖蛋白碳水化合物单元的酶促硫酸化作用:血型T抗原特异性及另外两种不同的Gal:3-O-磺基转移酶,从特异性、动力学以及碳水化合物链中硫酸根和岩藻糖残基对末端Gal的C-3硫酸化作用的影响方面得以明确。
Glycobiology. 1997 Sep;7(6):753-68. doi: 10.1093/glycob/7.6.753.
3
Identification of physiologically relevant substrates for cloned Gal: 3-O-sulfotransferases (Gal3STs): distinct high affinity of Gal3ST-2 and LS180 sulfotransferase for the globo H backbone, Gal3ST-3 for N-glycan multiterminal Galbeta1, 4GlcNAcbeta units and 6-sulfoGalbeta1, 4GlcNAcbeta, and Gal3ST-4 for the mucin core-2 trisaccharide.克隆的半乳糖:3 - O - 磺基转移酶(Gal3STs)的生理相关底物的鉴定:Gal3ST - 2和LS180磺基转移酶对球节H骨架具有不同的高亲和力,Gal3ST - 3对N - 聚糖多末端Galβ1,4GlcNAcβ单元和6 - 磺基Galβ1,4GlcNAcβ具有高亲和力,Gal3ST - 4对粘蛋白核心 - 2三糖具有高亲和力。
J Biol Chem. 2004 Mar 12;279(11):10032-41. doi: 10.1074/jbc.M311989200. Epub 2003 Dec 29.
4
Synthesis of alpha-D-galactopyranosyl-linked oligosaccharides containing the alpha-Gal-->beta-Gal-->GlcNAc sequence employing methyl-2,3,4,6-tetra-O-(4-methoxybenzyl)-1-thio-beta-D-galactopyranosid e as an efficient glycosyl donor.以甲基-2,3,4,6-四-O-(4-甲氧基苄基)-1-硫代-β-D-吡喃半乳糖苷作为高效糖基供体合成含有α-Gal→β-Gal→GlcNAc序列的α-D-吡喃半乳糖基连接的寡糖。
Carbohydr Res. 1994 Oct 3;263(1):67-77. doi: 10.1016/0008-6215(94)00153-7.
5
Synthesis of fluorinated mucin core 2 branched oligosaccharides with the potential of novel substrates and enzyme inhibitors for glycosyltransferases and sulfotransferases.具有作为糖基转移酶和磺基转移酶新型底物及酶抑制剂潜力的氟化粘蛋白核心2分支寡糖的合成。
J Org Chem. 2006 May 12;71(10):3696-706. doi: 10.1021/jo052626j.
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Synthesis of precursors for the dimeric 3-O-SO3Na Lewis X and Lewis A structures.
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Biochemistry. 1996 Jul 9;35(27):8914-24. doi: 10.1021/bi952193m.
8
Enzymatic midchain branching of polylactosamine backbones is restricted in a site-specific manner in alpha 1,3-fucosylated chains.在α1,3-岩藻糖基化链中,多乳糖胺主链的酶促中链分支以位点特异性方式受到限制。
Biochemistry. 1997 Nov 4;36(44):13729-35. doi: 10.1021/bi9712807.
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Sulfation of sialyl N-acetyllactosamine oligosaccharides and fetuin oligosaccharides by keratan sulfate Gal-6-sulfotransferase.硫酸角质素Gal-6-磺基转移酶对唾液酸N-乙酰乳糖胺寡糖和胎球蛋白寡糖的硫酸化作用。
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引用本文的文献

1
Novel interactions of complex carbohydrates with peanut (PNA), Ricinus communis (RCA-I), Sambucus nigra (SNA-I) and wheat germ (WGA) agglutinins as revealed by the binding specificities of these lectins towards mucin core-2 O-linked and N-linked glycans and related structures.通过这些凝集素对粘蛋白核心2 O-连接和N-连接聚糖及相关结构的结合特异性揭示复杂碳水化合物与花生凝集素(PNA)、蓖麻凝集素(RCA-I)、黑接骨木凝集素(SNA-I)和麦胚凝集素(WGA)的新型相互作用。
Glycoconj J. 2016 Oct;33(5):819-36. doi: 10.1007/s10719-016-9678-y. Epub 2016 Jun 18.
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Reversible sialylation: synthesis of cytidine 5'-monophospho-N-acetylneuraminic acid from cytidine 5'-monophosphate with alpha2,3-sialyl O-glycan-, glycolipid-, and macromolecule-based donors yields diverse sialylated products.可逆唾液酸化:以α2,3-唾液酸基O-聚糖、糖脂和大分子为供体,从5'-单磷酸胞苷合成5'-单磷酸胞苷-N-乙酰神经氨酸,可产生多种唾液酸化产物。
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本文引用的文献

1
Synthesis of oligosaccharides containing beta-D-Gal-(1-->3)-O-(6-O-sulfo-beta-D-GlcNAc) as a terminal unit.
Carbohydr Res. 1998 Sep;311(3):165-9. doi: 10.1016/s0008-6215(98)00166-9.
2
The enzymatic sulfation of glycoprotein carbohydrate units: blood group T-hapten specific and two other distinct Gal:3-O-sulfotransferases as evident from specificities and kinetics and the influence of sulfate and fucose residues occurring in the carbohydrate chain on C-3 sulfation of terminal Gal.糖蛋白碳水化合物单元的酶促硫酸化作用:血型T抗原特异性及另外两种不同的Gal:3-O-磺基转移酶,从特异性、动力学以及碳水化合物链中硫酸根和岩藻糖残基对末端Gal的C-3硫酸化作用的影响方面得以明确。
Glycobiology. 1997 Sep;7(6):753-68. doi: 10.1093/glycob/7.6.753.
3
Specificity analysis of three clonal and five non-clonal alpha 1,3-L-fucosyltransferases with sulfated, sialylated, or fucosylated synthetic carbohydrates as acceptors in relation to the assembly of 3'-sialyl-6'-sulfo Lewis x (the L-selectin ligand) and related complex structures.
3
Characterization of distinct Gal:3-O-sulfotransferase activities in human tumor epithelial cell lines and of calf lymph node GlcNAc : 6-O-sulfotransferase activity.人肿瘤上皮细胞系中不同的半乳糖:3-O-磺基转移酶活性及小牛淋巴结N-乙酰葡糖胺:6-O-磺基转移酶活性的鉴定
Glycoconj J. 1999 Sep;16(9):523-36. doi: 10.1023/a:1007074005371.
以硫酸化、唾液酸化或岩藻糖基化的合成碳水化合物作为受体,对三种克隆型和五种非克隆型α1,3-L-岩藻糖基转移酶进行特异性分析,分析其与3'-唾液酸基-6'-磺酸基路易斯x(L-选择素配体)及相关复杂结构组装的关系。
Biochemistry. 1996 Jul 9;35(27):8925-33. doi: 10.1021/bi952194e.
4
Characterization of the specificities of human blood group H gene-specified alpha 1,2-L-fucosyltransferase toward sulfated/sialylated/fucosylated acceptors: evidence for an inverse relationship between alpha 1,2-L-fucosylation of Gal and alpha 1,6-L-fucosylation of asparagine-linked GlcNAc.人类血型H基因指定的α1,2-L-岩藻糖基转移酶对硫酸化/唾液酸化/岩藻糖基化受体的特异性表征:Gal的α1,2-L-岩藻糖基化与天冬酰胺连接的GlcNAc的α1,6-L-岩藻糖基化之间呈负相关的证据。
Biochemistry. 1996 Jul 9;35(27):8914-24. doi: 10.1021/bi952193m.
5
Complex-type N-linked oligosaccharides of gp120 from human immunodeficiency virus type 1 contain sulfated N-acetylglucosamine.来自1型人类免疫缺陷病毒的gp120的复合型N-连接寡糖含有硫酸化的N-乙酰葡糖胺。
J Virol. 1993 Feb;67(2):943-52. doi: 10.1128/JVI.67.2.943-952.1993.
6
A convenient synthesis of N-acetyllactosamine-linked oligosaccharides from phenyl 3,6,2',3',4',6'-hexa-O-acetyl-2-deoxy-2-phthalimido-1-thio-beta-lactopy ranoside .
Carbohydr Res. 1993 May 7;243(2):385-91. doi: 10.1016/0008-6215(93)87042-q.
7
6'-sulfated sialyl Lewis x is a major capping group of GlyCAM-1.6'-硫酸化唾液酸化路易斯x是糖基化细胞粘附分子-1的主要封端基团。
Biochemistry. 1994 Apr 26;33(16):4830-5. doi: 10.1021/bi00182a011.
8
Synthesis of alpha-D-galactopyranosyl-linked oligosaccharides containing the alpha-Gal-->beta-Gal-->GlcNAc sequence employing methyl-2,3,4,6-tetra-O-(4-methoxybenzyl)-1-thio-beta-D-galactopyranosid e as an efficient glycosyl donor.以甲基-2,3,4,6-四-O-(4-甲氧基苄基)-1-硫代-β-D-吡喃半乳糖苷作为高效糖基供体合成含有α-Gal→β-Gal→GlcNAc序列的α-D-吡喃半乳糖基连接的寡糖。
Carbohydr Res. 1994 Oct 3;263(1):67-77. doi: 10.1016/0008-6215(94)00153-7.
9
Synthesis of benzyl O-(3-O-methyl-beta-D-galactopyranosyl)-(1-->3)-2- acetamido-2-deoxy-alpha-D-galactopyranoside and benzyl O-(beta-D- galactopyranosyl)-(1-->3)-2-acetamido-2-deoxy-6-O-methyl-alpha-D- galactopyranoside as specific acceptors for sialyltransferases.合成苄基O-(3-O-甲基-β-D-吡喃半乳糖基)-(1→3)-2-乙酰氨基-2-脱氧-α-D-吡喃半乳糖苷和苄基O-(β-D-吡喃半乳糖基)-(1→3)-2-乙酰氨基-2-脱氧-6-O-甲基-α-D-吡喃半乳糖苷作为唾液酸转移酶的特异性受体。
Carbohydr Res. 1995 Jul 11;271(2):247-51. doi: 10.1016/0008-6215(95)00072-2.
10
Selectin ligands and tumor-associated carbohydrate structures: specificities of alpha 2,3-sialyltransferases in the assembly of 3'-sialyl-6-sialyl/sulfo Lewis a and x, 3'-sialyl-6'-sulfo Lewis x, and 3'-sialyl-6-sialyl/sulfo blood group T-hapten.选择素配体与肿瘤相关碳水化合物结构:α2,3-唾液酸转移酶在3'-唾液酸-6-唾液酸/磺酸化路易斯a和x、3'-唾液酸-6'-磺酸化路易斯x以及3'-唾液酸-6-唾液酸/磺酸化血型T抗原组装中的特异性
Biochemistry. 1995 Mar 7;34(9):2925-36. doi: 10.1021/bi00009a024.