5-(hydrazinocarbonyl)pentyl α-L-rhamnopyranosyl-(1->2)-O-α-D-galactopyranosyl-(1->3)-(2-acetamido-2-deoxy-α-D-glucopyranosyl)-(1->3)-α-L-rhamnopyranoside | 213185-49-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(hydrazinocarbonyl)pentyl α-L-rhamnopyranosyl-(1->2)-O-α-D-galactopyranosyl-(1->3)-(2-acetamido-2-deoxy-α-D-glucopyranosyl)-(1->3)-α-L-rhamnopyranoside
• 英文别名: N-[(2R,3R,4R,5S,6R)-4-[(2S,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-2-[(2R,3R,4R,5S,6S)-2-(6-hydrazinyl-6-oxohexoxy)-3,5-dihydroxy-6-methyloxan-4-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• CAS: 213185-49-0
• 化学式: C₃₂H₅₇N₃O₂₀
• 分子量: 803.813
• InChiKey: QBQRKPDXBWMZHX-QLUSINOTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.3
• 重原子数：
  55
• 可旋转键数：
  16
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  360
• 氢给体数：
  13
• 氢受体数：
  21

反应信息

• 作为反应物：
  描述：

  5-(hydrazinocarbonyl)pentyl α-L-rhamnopyranosyl-(1->2)-O-α-D-galactopyranosyl-(1->3)-(2-acetamido-2-deoxy-α-D-glucopyranosyl)-(1->3)-α-L-rhamnopyranoside 在 溶剂黄146 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成
  参考文献：
  名称：

  Synthesis of Glycoconjugate Vaccines against Shigella dysenteriae Type 1

  摘要：

  Syntheses of a hexadecasaccharide and smaller fragments corresponding to one-four repeating units of the O-specific polysaccharide of Shigella dysenteriae type 1 are reported in a reactive aglyconlinked from. Two tetrasaccharide donor/acceptor repeating units were assembled from monosaccharide precursors in a stepwise fashion and used in a linear, iterative manner to construct the higher-membered saccharides using Schmidt's glycosylation technique that proved superior to others tested. Single-point attachment of the saccharides to human serum albumin, using a secondary heterobifunctional spacer, afforded a range of glycoconjugates for a detailed evaluation of their immunological characteristics.

  DOI：

  10.1021/jo980660a
• 作为产物：
  描述：

  在 palladium on activated charcoal 氢气 、 肼 作用下， 以 甲醇 、 乙醇 、 溶剂黄146 为溶剂， 23.0 ℃ 、1.38 MPa 条件下， 反应 192.0h， 生成 5-(hydrazinocarbonyl)pentyl α-L-rhamnopyranosyl-(1->2)-O-α-D-galactopyranosyl-(1->3)-(2-acetamido-2-deoxy-α-D-glucopyranosyl)-(1->3)-α-L-rhamnopyranoside
  参考文献：
  名称：

  Synthesis of Glycoconjugate Vaccines against Shigella dysenteriae Type 1

  摘要：

  Syntheses of a hexadecasaccharide and smaller fragments corresponding to one-four repeating units of the O-specific polysaccharide of Shigella dysenteriae type 1 are reported in a reactive aglyconlinked from. Two tetrasaccharide donor/acceptor repeating units were assembled from monosaccharide precursors in a stepwise fashion and used in a linear, iterative manner to construct the higher-membered saccharides using Schmidt's glycosylation technique that proved superior to others tested. Single-point attachment of the saccharides to human serum albumin, using a secondary heterobifunctional spacer, afforded a range of glycoconjugates for a detailed evaluation of their immunological characteristics.

  DOI：

  10.1021/jo980660a

文献信息

• A New Method for Conjugation of Carbohydrates to Proteins Using an Aminooxy-Thiol Heterobifunctional Linker
  作者：Joanna Kubler-Kielb、Vince Pozsgay

  DOI：10.1021/jo050934b

  日期：2005.8.1

  A new, efficient, and mild protocol is presented for the coupling of saccharides to proteins. First, a heterobifunctional aminooxy-thiol linker is coupled to the bromoacylated protein to introduce aminooxy groups through thioether linkages. Condensation of the aminooxylated protein and aldehydo/keto-derivatized carbohydrates affords covalent saccharide−protein constructs. Uncoupled saccharide can be

  提出了一种新的，有效的，温和的方案，用于糖与蛋白质的偶联。首先，将异双功能氨基氧基-硫醇接头与溴酰化的蛋白质偶联，以通过硫醚键引入氨基氧基。氨基氧化蛋白和醛/酮衍生的碳水化合物的缩合提供共价糖蛋白构建体。未偶联的糖可以其原始形式回收。我们的方案的范围以中性单糖和四糖以及带负电荷的核糖醇磷酸酯构建体与BSA的偶联为例。
• Synthesis of Glycoconjugate Vaccines against <i>Shigella dysenteriae</i> Type 1
  作者：Vince Pozsgay

  DOI：10.1021/jo980660a

  日期：1998.8.1

  Syntheses of a hexadecasaccharide and smaller fragments corresponding to one-four repeating units of the O-specific polysaccharide of Shigella dysenteriae type 1 are reported in a reactive aglyconlinked from. Two tetrasaccharide donor/acceptor repeating units were assembled from monosaccharide precursors in a stepwise fashion and used in a linear, iterative manner to construct the higher-membered saccharides using Schmidt's glycosylation technique that proved superior to others tested. Single-point attachment of the saccharides to human serum albumin, using a secondary heterobifunctional spacer, afforded a range of glycoconjugates for a detailed evaluation of their immunological characteristics.