3-(2-Aminoethylthio)propyl (β-D-glucopyranosyluronic acid)-(1->3)-(2-acetamido-2-deoxy-β-D-galactopyranosyl)-(1->6)-[(β-D-glucopyranosyluronic acid)-(1->3)]-2-acetamido-2-deoxy-β-D-galactopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(2-Aminoethylthio)propyl (β-D-glucopyranosyluronic acid)-(1->3)-(2-acetamido-2-deoxy-β-D-galactopyranosyl)-(1->6)-[(β-D-glucopyranosyluronic acid)-(1->3)]-2-acetamido-2-deoxy-β-D-galactopyranoside
• 英文别名: (2S,3S,4S,5R,6R)-6-[(2R,3R,4R,5R,6R)-3-acetamido-2-[[(2R,3R,4R,5R,6R)-5-acetamido-6-[3-(2-aminoethylsulfanyl)propoxy]-4-[(2R,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy-3-hydroxyoxan-2-yl]methoxy]-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
• 化学式: C₃₃H₅₅N₃O₂₃S
• 分子量: 893.872
• InChiKey: AYBNRJUUCOBXBA-AIPWVCDHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -9.1
• 重原子数：
  60
• 可旋转键数：
  19
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  440
• 氢给体数：
  14
• 氢受体数：
  25

反应信息

• 作为反应物：
  描述：

  方酸二乙酯 、 3-(2-Aminoethylthio)propyl (β-D-glucopyranosyluronic acid)-(1->3)-(2-acetamido-2-deoxy-β-D-galactopyranosyl)-(1->6)-[(β-D-glucopyranosyluronic acid)-(1->3)]-2-acetamido-2-deoxy-β-D-galactopyranoside 在 sodium phosphate buffer 作用下， 以 乙醇 为溶剂， 生成 3-{2-[N-(2-Ethoxy-3,4-dioxocyclobut-1-enyl)amino]ethylthio}propyl (β-D-glucopyranosyluronic acid)-(1->3)-(2-acetamido-2-deoxy-β-D-galactopyranosyl)-(1->6)-[(β-D-glucopyranosyluronic acid)-(1->3)]-2-acetamido-2-deoxy-β-D-galactopyranoside
  参考文献：
  名称：

  与曼氏血吸虫寄生虫循环阳极抗原的免疫反应部分有关的寡糖片段的合成和缀合

  摘要：

  循环阳极的免疫反应部分 抗原从寄生虫（CAA）曼氏血吸虫是一个苏氨酸链接 多糖由→6）-[β- D -Glc p A-（1→3）]-β- D- Gal p NAc-（1→重复组成二糖。在免疫化学项目的框架内，作为早期合成二四糖CAA片段，含间隔物的五糖片段的合成，3-（2-氨基乙硫基）丙基（2-乙酰氨基-2-脱氧-β - D-吡喃半乳糖基）-（1→6）-[（β- D-吡喃葡糖基糖醛酸）酸）-（1→3）]-（2-乙酰氨基-2-脱氧-β - D-吡喃半乳糖基）-（1→6）-[（β- D-吡喃葡糖基糖醛酸）-（1→3）]-2描述了-乙酰氨基-2-脱氧-β - D-吡喃半乳糖苷。此外，合成了1- O- [3-（2-氨基乙硫基）丙基] -N-乙酰基-β - D-半乳糖胺。氧化作用 三元合成的步骤 五糖 使用重铬酸吡啶鎓和 醋酸酐。TEMPO催化的氧化反应在合成中得到了探索。1 - O- [6-氨基己基]-β-

  DOI：

  10.1039/b002083o
• 作为产物：
  描述：

  allyl (β-D-glucopyranosyluronic acid)-(1->3)-(2-amino-2-deoxy-β-D-galactopyranosyl)-(1->6)-[(β-D-glucopyranosyluronic acid)-(1->3)]-2-amino-2-deoxy-β-D-galactopyranoside 以 甲醇 、 水 为溶剂， 反应 2.0h， 生成 3-(2-Aminoethylthio)propyl (β-D-glucopyranosyluronic acid)-(1->3)-(2-acetamido-2-deoxy-β-D-galactopyranosyl)-(1->6)-[(β-D-glucopyranosyluronic acid)-(1->3)]-2-acetamido-2-deoxy-β-D-galactopyranoside
  参考文献：
  名称：

  Preparation of spacer-containing di-, tri-, and tetrasaccharide fragments of the circulating anodic antigen of Schistosoma mansoni for diagnostic purposes

  摘要：

  The chemical synthesis of beta-D-GlcpA-(1 --> 3)-beta-D-GalpNAc-(1 --> O)CH2CH = CH2, beta-D-GalpNAc-(1 --> 6)-[beta-D-GlcpA-(1 --> 3)]-beta-D-GalpNAc-(1 --> O)CH2CH = CH2, and beta-D-GlcpA-(1 --> 3)-beta-D-GalpNAc-(1 --> 6)-[beta-D-GlcpA-(1 --> 3)]-beta-D-GalpNAc-(1 --> O)CH2CH = CH2 is described. These oligosaccharides represent fragments of the circulating anodic antigen, secreted by the parasite Schistosoma mansoni in the circulatory system of the host. The applied synthesis strategy includes the preparation of a non-oxidised backbone oligosaccharide, with a levulinoyl group at O-6 of the beta-D-glucose residue. After the selective removal of the levulinoyl group, the obtained hydroxyl functions were converted into carboxyl groups, using pyridinium dichromate and acetic anhydride in dichloromethane, to afford the desired glucuronic-acid-containing oligosaccharides. Subsequently, the allyl glycosides have been elongated with cysteamine to give the corresponding aminespacer-containing oligosaccharides. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00125-6

文献信息

• Synthesis and conjugation of oligosaccharide fragments related to the immunologically reactive part of the circulating anodic antigen of the parasite Schistosoma mansoni
  作者：Henricus J. Vermeer、Koen M. Halkes、J. Albert van Kuik、Johannis P. Kamerling、Johannes F. G. Vliegenthart

  DOI：10.1039/b002083o

  日期：——

  l (2-acetamido-2-deoxy-β-D-galactopyranosyl)-(1→6)-[(β-D-glucopyranosyluronic acid)-(1→3)]-(2-acetamido-2-deoxy-β-D-galactopyranosyl)-(1→6)-[(β-D-glucopyranosyluronic acid)-(1→3)]-2-acetamido-2-deoxy-β-D-galactopyranoside, is described. Moreover, 1-O-[3-(2-aminoethylthio)propyl]-N-acetyl-β-D-galactosamine was synthesized. Oxidation steps in the synthesis of tri- to pentasaccharide CAA fragments were

  循环阳极的免疫反应部分 抗原从寄生虫（CAA）曼氏血吸虫是一个苏氨酸链接 多糖由→6）-[β- D -Glc p A-（1→3）]-β- D- Gal p NAc-（1→重复组成二糖。在免疫化学项目的框架内，作为早期合成二四糖CAA片段，含间隔物的五糖片段的合成，3-（2-氨基乙硫基）丙基（2-乙酰氨基-2-脱氧-β - D-吡喃半乳糖基）-（1→6）-[（β- D-吡喃葡糖基糖醛酸）酸）-（1→3）]-（2-乙酰氨基-2-脱氧-β - D-吡喃半乳糖基）-（1→6）-[（β- D-吡喃葡糖基糖醛酸）-（1→3）]-2描述了-乙酰氨基-2-脱氧-β - D-吡喃半乳糖苷。此外，合成了1- O- [3-（2-氨基乙硫基）丙基] -N-乙酰基-β - D-半乳糖胺。氧化作用 三元合成的步骤 五糖 使用重铬酸吡啶鎓和 醋酸酐。TEMPO催化的氧化反应在合成中得到了探索。1 - O- [6-氨基己基]-β-
• Preparation of spacer-containing di-, tri-, and tetrasaccharide fragments of the circulating anodic antigen of Schistosoma mansoni for diagnostic purposes
  作者：Koen M Halkes、Henricus J Vermeer、Ted M Slaghek、Peter A.V van Hooft、Arnoud Loof、Johannis P Kamerling、Johannes F.G Vliegenthart

  DOI：10.1016/s0008-6215(98)00125-6

  日期：1998.5

  The chemical synthesis of beta-D-GlcpA-(1 --> 3)-beta-D-GalpNAc-(1 --> O)CH2CH = CH2, beta-D-GalpNAc-(1 --> 6)-[beta-D-GlcpA-(1 --> 3)]-beta-D-GalpNAc-(1 --> O)CH2CH = CH2, and beta-D-GlcpA-(1 --> 3)-beta-D-GalpNAc-(1 --> 6)-[beta-D-GlcpA-(1 --> 3)]-beta-D-GalpNAc-(1 --> O)CH2CH = CH2 is described. These oligosaccharides represent fragments of the circulating anodic antigen, secreted by the parasite Schistosoma mansoni in the circulatory system of the host. The applied synthesis strategy includes the preparation of a non-oxidised backbone oligosaccharide, with a levulinoyl group at O-6 of the beta-D-glucose residue. After the selective removal of the levulinoyl group, the obtained hydroxyl functions were converted into carboxyl groups, using pyridinium dichromate and acetic anhydride in dichloromethane, to afford the desired glucuronic-acid-containing oligosaccharides. Subsequently, the allyl glycosides have been elongated with cysteamine to give the corresponding aminespacer-containing oligosaccharides. (C) 1998 Elsevier Science Ltd. All rights reserved.