3-(2-aminoethylthio)propyl-3-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-2-O-{3-O-[3-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-2-O-(α-L-rhamnopyranosyl)-α-L-rhamnopyranosyl]-α-L-rhamnopyranosyl}-α-L-rhamnopyranoside | 187221-47-2

• 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-3-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-2-O-{3-O-[3-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-2-O-(α-L-rhamnopyranosyl)-α-L-rhamnopyranosyl]-α-L-rhamnopyranosyl}-α-L-rhamnopyranoside
• CAS: 187221-47-2
• 化学式: C₄₅H₇₉N₃O₂₇S
• 分子量: 1126.19
• InChiKey: ZZIBKABEKPDAHU-FVUDBDPOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -8.6
• 重原子数：
  76.0
• 可旋转键数：
  21.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  457.97
• 氢给体数：
  16.0
• 氢受体数：
  29.0

反应信息

• 作为反应物：
  描述：

  方酸二乙酯 、 3-(2-aminoethylthio)propyl-3-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-2-O-{3-O-[3-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-2-O-(α-L-rhamnopyranosyl)-α-L-rhamnopyranosyl]-α-L-rhamnopyranosyl}-α-L-rhamnopyranoside 以 甲醇 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  Synthesis and immunological activity of an oligosaccharide-conjugate as a vaccine candidate against Group A Streptococcus

  摘要：

  The synthesis and immunogenicity of a tetanus toxoid (TT)-conjugate of the hexasaccharide portion of the cell-wall polysaccharide (CWPS) of the Group A Streptococcus (GAS) is described. The synthesis relies on the reaction of an allyl glycoside of the hexasaccharide with cysteamine, followed by the reaction of the resultant amine with diethyl squarate to give the monoethyl squarate adduct. Subsequent reaction with the lysine epsilon-amino groups on TT gives the glycoconjugate containing 30 hexasaccharide haptens per TT molecule. The immunogenicity in mice is similar to that obtained with a native CWPS-TT conjugate, validating the glycoconjugate as a vaccine candidate against GAS infections. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.09.042
• 作为产物：
  描述：

  半胱胺盐酸盐 、 以 水 为溶剂， 反应 0.83h， 以82%的产率得到3-(2-aminoethylthio)propyl-3-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-2-O-{3-O-[3-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-2-O-(α-L-rhamnopyranosyl)-α-L-rhamnopyranosyl]-α-L-rhamnopyranosyl}-α-L-rhamnopyranoside
  参考文献：
  名称：

  Preparation of antigens and immunoadsorbents corresponding to the Streptococcus group a cell-wall polysaccharide

  摘要：

  The allyl glycosides of a tri-, penta- and hexasaccharide corresponding to the Streptococcus Group A cell-wall polysaccharide were coupled to solid or soluble supports to give immunoaffinity columns and neoglycoproteins, respectively. Cysteamine hydrochloride was added to the allyl glycosides and the resulting cysteamine adducts were used for subsequent coupling to linkers via the amine functionality. The tri- and penta- saccharide cysteamine adducts were coupled directly to the azalactone-derivatized 3M Emphase(TM) Biosupport Medium AB 1 to yield two affinity columns. The penta- and hexa- saccharides were coupled to bovine serum albumin or ovalbumin via the conjugate addition of the E-amino groups of lysines on the proteins with the N-acryloylated sugars or the oligosaccharide-squarate adducts, derived in turn from the cysteamine adducts. The efficiency of the above methods is compared. Copyright (C) 1996 Published by Elsevier Science Ltd

  DOI：

  10.1016/s0968-0896(96)00183-6