(methyl-2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-(1->4)-2-acetamido-1,3,6-tri-O-acetyl-2-deoxy-α-D-glucopyranose | 824958-68-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (methyl-2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-(1->4)-2-acetamido-1,3,6-tri-O-acetyl-2-deoxy-α-D-glucopyranose
• 英文别名: methyl (2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-(1→4)-2-acetamido-1,3,6-tri-O-acetyl-2-deoxy-α-D-glucopyranoside
• CAS: 824958-68-1
• 化学式: C₂₇H₃₇NO₁₈
• 分子量: 663.587
• InChiKey: GNSAGKCTVQFZIM-QOHHZPLDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.65
• 重原子数：
  46.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  240.89
• 氢给体数：
  1.0
• 氢受体数：
  18.0

反应信息

• 作为反应物：
  描述：

  (methyl-2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-(1->4)-2-acetamido-1,3,6-tri-O-acetyl-2-deoxy-α-D-glucopyranose 在 Carbonate buffer 、 三氟甲磺酸三甲基硅酯 、 chitinase from Bacillus sp 、 sodium methylate 作用下， 以 甲醇 、 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 8.5h， 生成 methyl (sodium β-D-glucopyranosyluronate)-(1->4)-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->4)-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Enzymatic glycosidation of sugar oxazolines having a carboxylate group catalyzed by chitinase

  摘要：

  Enzymatic glycosidation using sugar oxazolines 1-3 having a carboxylate group as glycosyl donors and compounds 4-6 as glycosyl acceptors was performed by employing a chitinase from Bacillus sp. as catalyst. All the glycosidations proceeded with full control in stereochemistry at the anomeric carbon of the donor and regio-selectivity of the acceptor. The N,N'-diacetyl-6'-O-carboxymethyl chitobiose oxazoline derivative 1 was effectively glycosidated, under catalysis by the enzyme, with methyl N,N'-diacetyl-beta-chitobioside (4), pent-4-enyl N-acetyl-beta-D-glucosaminide (5), and methyl N-acetyl-beta-D-glucosaminide (6), affording in good yields the corresponding oligosaccharide derivatives having 6-O-carboxymethyl group at the nonreducing GlcNAc residue. The N,N'-diacetyl-6-O-carboxymethylchitobiose oxazoline derivative 2 was subjected to catalysis by the enzyme catalysis; however, no glycosidated products were produced through the reactions with 4, 5, and 6. Glycosidation reactions of the beta-D-glycosyluronic(1-->4)-N-acetyl-D-glucosamine oxazoline derivative 3 proceeded with each of the glycosyl acceptors, giving rise to the corresponding oligosaccharide derivative having a GlcA residue at their nonreducing termini in good yields. (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.carres.2004.08.016
• 作为产物：
  描述：

  3,4,6-三邻乙酰基-alpha-D-吡喃葡萄糖 1,2-(原酸甲酯) 、 (+)-2-acetamido-1,3,6-tri-O-acetyl-2-deoxy-α-D-glucopyranoside 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以51%的产率得到(methyl-2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-(1->4)-2-acetamido-1,3,6-tri-O-acetyl-2-deoxy-α-D-glucopyranose
  参考文献：
  名称：

  Enzymatic glycosidation of sugar oxazolines having a carboxylate group catalyzed by chitinase

  摘要：

  Enzymatic glycosidation using sugar oxazolines 1-3 having a carboxylate group as glycosyl donors and compounds 4-6 as glycosyl acceptors was performed by employing a chitinase from Bacillus sp. as catalyst. All the glycosidations proceeded with full control in stereochemistry at the anomeric carbon of the donor and regio-selectivity of the acceptor. The N,N'-diacetyl-6'-O-carboxymethyl chitobiose oxazoline derivative 1 was effectively glycosidated, under catalysis by the enzyme, with methyl N,N'-diacetyl-beta-chitobioside (4), pent-4-enyl N-acetyl-beta-D-glucosaminide (5), and methyl N-acetyl-beta-D-glucosaminide (6), affording in good yields the corresponding oligosaccharide derivatives having 6-O-carboxymethyl group at the nonreducing GlcNAc residue. The N,N'-diacetyl-6-O-carboxymethylchitobiose oxazoline derivative 2 was subjected to catalysis by the enzyme catalysis; however, no glycosidated products were produced through the reactions with 4, 5, and 6. Glycosidation reactions of the beta-D-glycosyluronic(1-->4)-N-acetyl-D-glucosamine oxazoline derivative 3 proceeded with each of the glycosyl acceptors, giving rise to the corresponding oligosaccharide derivative having a GlcA residue at their nonreducing termini in good yields. (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.carres.2004.08.016

文献信息

• [EN] SYNTHESIS OF DISACCHARIDE BLOCKS FROM NATURAL POLYSACCHARIDES FOR HEPARAN SULFATE OLIGOSACCHARIDE ASSEMBLY<br/>[FR] SYNTHÈSE DE BLOCS DE DISACCHARIDE À PARTIR DE POLYSACCHARIDES NATURELS POUR ASSEMBLAGE D'OLIGOSACCHARIDE DE TYPE SULFATE D'HÉPARANE
  申请人：CALIFORNIA INST OF TECHN

  公开号：WO2020132625A1

  公开（公告）日：2020-06-25

  Methods for the preparation of oligosaccharide products from polysaccharide starting materials are disclosed. The methods include: hydrolyzing a glucosamine-containing polysaccharide starting material, such as heparin or heparosan, under conditions sufficient to form an oligosaccharide intermediate (e.g., a GlcN-IdoA disaccharide intermediate or a GlcA-GlcN disaccharide intermediate), and converting the oligosaccharide intermediate to the oligosaccharide product. Conversion of the oligosaccharide intermediates to the oligosaccharide products may include one or more esterification, acylation, epimerization, protection, and deprotection steps. Preparation of higher-order oligomers is described, as well as methods for selective oligosaccharide sulfation.

  揭示了从多糖起始材料制备寡糖产物的方法。这些方法包括：在足以形成寡糖中间体（例如GlcN-IdoA二糖中间体或GlcA-GlcN二糖中间体）的条件下水解含有葡萄糖胺的多糖起始材料，然后将寡糖中间体转化为寡糖产物。将寡糖中间体转化为寡糖产物可能包括一个或多个酯化、酰化、差向异构化、保护和去保护步骤。描述了更高阶寡聚体的制备方法，以及选择性寡糖硫酸化的方法。
• Expedient Synthesis of Core Disaccharide Building Blocks from Natural Polysaccharides for Heparan Sulfate Oligosaccharide Assembly
  作者：Nitin J. Pawar、Lei Wang、Takuya Higo、Chandrabali Bhattacharya、Pavan K. Kancharla、Fuming Zhang、Kedar Baryal、Chang‐Xin Huo、Jian Liu、Robert J. Linhardt、Xuefei Huang、Linda C. Hsieh‐Wilson

  DOI：10.1002/anie.201908805

  日期：2019.12.16

  HS structures. Herein, we describe a new approach to access the four core disaccharides required for HS/heparin oligosaccharide assembly from natural polysaccharides. The use of disaccharides rather than monosaccharides as minimal precursors greatly accelerates the synthesis of HS GAGs, providing key disaccharide and tetrasaccharide intermediates in about half the number of steps compared to traditional

  硫酸乙酰肝素糖胺聚糖（HS GAG）的复杂硫酸化基序在许多重要的生物学过程中起着至关重要的作用。但是，由于无法合成大量不同的，但已定义的HS结构，因此妨碍了对它们特定功能的理解。在这里，我们描述了一种从天然多糖中获取HS /肝素寡糖组装所需的四个核心二糖的新方法。使用二糖而不是单糖作为最少的前体极大地加快了HS GAG的合成，与传统方法相比，只需约一半的步骤即可提供关键的二糖和四糖中间体。快速获得此类多功能中间体将使能够生成全面的硫酸盐寡糖文库，从而解锁“