3-azidopropyl (2-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzoyl-β-D-glucopyranosyl)-(1->3)-(2-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzoyl-β-D-glucopyranoside | 400865-24-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-azidopropyl (2-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzoyl-β-D-glucopyranosyl)-(1->3)-(2-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzoyl-β-D-glucopyranoside
• CAS: 400865-24-9
• 化学式: C₉₇H₈₇N₃O₂₉
• 分子量: 1758.76
• InChiKey: RJXVYOQZQPFFJQ-WUIFZNQKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.42
• 重原子数：
  129.0
• 可旋转键数：
  31.0
• 环数：
  16.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  390.15
• 氢给体数：
  1.0
• 氢受体数：
  30.0

反应信息

• 作为反应物：
  描述：

  3-azidopropyl (2-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzoyl-β-D-glucopyranosyl)-(1->3)-(2-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzoyl-β-D-glucopyranoside 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以70%的产率得到3-azidopropyl (2-O-benzoyl-β-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzoyl-β-D-glucopyranosyl)-(1->3)-(2-O-benzoyl-β-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzoyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis ofStreptococcus pneumoniae Type 3 Neoglycoproteins Varying in Oligosaccharide Chain Length, Loading and Carrier Protein

  摘要：

  The preparation is described of a range of neoglycoproteins containing synthesised fragments of the capsular polysaccharide of Streptococcus pneumoniae type 3, that is beta-D-GlcpA-(1-->4)-beta-D-Glcp-(1-->O)-(CH2)3NH2 (1), beta-D-Glcp-(1-->3)-beta-D-GlcpA-(1-->4)-beta-D-Glcp-(1-->O)-(CH2)3NH2 (2), and beta-D-GlcpA-(1-->4)-beta-D-Glcp-(1-->3)-beta-D-GlcpA-(1-->4)-beta-D-Glcp-(1-->O)-(CH4)NH2 (3). A blockwise approach was developed for the synthesis of the protected carbohydrate chains, in which the carboxylic groups were introduced prior to deprotection by selective oxidation of HO-6 in the presence of HO-4 by using TEMPO (2,2,6,6-tetramethyl-1-piperidinyloxy radical). After deprotection, the 3-aminopropyl spacer of the fragments was elongated with diethyl squarate (3,4-diethoxy-3-cyclobutene-1,2-dione) and the elongated oligosaccharides were conjugated to CRM197 (cross-reacting material of diphtheria toxin), KLH (keyhole limpet hemocyanin) or TT (tetanus toxoid). The resulting neoglycoconjugates varied in oligosaccharide chain length, oligosaccharide loading and protein carrier. These well-defined conjugates are ideal probes for evaluating the influence of the different structural parameters in immunological tests.

  DOI：

  10.1002/1521-3765(20011015)7:20<4411::aid-chem4411>3.0.co;2-t
• 作为产物：
  描述：

  3-azidopropyl (2-O-benzoyl-4,6-O-benzylidene-3-O-chloroacetyl-β-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzoyl-β-D-glucopyranosyl)-(1->3)-(2-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzoyl-β-D-glucopyranoside 在 吡啶 、 硫脲 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以84%的产率得到3-azidopropyl (2-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzoyl-β-D-glucopyranosyl)-(1->3)-(2-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzoyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis ofStreptococcus pneumoniae Type 3 Neoglycoproteins Varying in Oligosaccharide Chain Length, Loading and Carrier Protein

  摘要：

  The preparation is described of a range of neoglycoproteins containing synthesised fragments of the capsular polysaccharide of Streptococcus pneumoniae type 3, that is beta-D-GlcpA-(1-->4)-beta-D-Glcp-(1-->O)-(CH2)3NH2 (1), beta-D-Glcp-(1-->3)-beta-D-GlcpA-(1-->4)-beta-D-Glcp-(1-->O)-(CH2)3NH2 (2), and beta-D-GlcpA-(1-->4)-beta-D-Glcp-(1-->3)-beta-D-GlcpA-(1-->4)-beta-D-Glcp-(1-->O)-(CH4)NH2 (3). A blockwise approach was developed for the synthesis of the protected carbohydrate chains, in which the carboxylic groups were introduced prior to deprotection by selective oxidation of HO-6 in the presence of HO-4 by using TEMPO (2,2,6,6-tetramethyl-1-piperidinyloxy radical). After deprotection, the 3-aminopropyl spacer of the fragments was elongated with diethyl squarate (3,4-diethoxy-3-cyclobutene-1,2-dione) and the elongated oligosaccharides were conjugated to CRM197 (cross-reacting material of diphtheria toxin), KLH (keyhole limpet hemocyanin) or TT (tetanus toxoid). The resulting neoglycoconjugates varied in oligosaccharide chain length, oligosaccharide loading and protein carrier. These well-defined conjugates are ideal probes for evaluating the influence of the different structural parameters in immunological tests.

  DOI：

  10.1002/1521-3765(20011015)7:20<4411::aid-chem4411>3.0.co;2-t

文献信息

• Synthesis of a hexasaccharide fragment of the capsular polysaccharide of <i>Streptococcus pneumoniae</i> type 3
  作者：Dirk J Lefeber、Eneko Aldaba Arévalo、Johannis P Kamerling、Johannes FG Vliegenthart

  DOI：10.1139/v01-190

  日期：2002.1.1

  In the framework of the development of a new generation of neoglycoconjugate vaccines against Streptococcus pneumoniae, the synthesis is described of a spacer-containing hexasaccharide fragment related to the capsular polysaccharide of S. pneumoniae type 3. Hexasaccharide β-D-GlcpA-(1[Formula: see text]4)-β-D-Glcp-(1[Formula: see text]3)-β-D-GlcpA-(1[Formula: see text]4)-β-D- Glcp-(1[Formula: see text]3)-β-D-GlcpA-(1[Formula: see text]4)-β-D-Glcp-(1[Formula: see text]O-(CH₂)₃NH₂) (1), comprised of three repeating units, was synthesized via a blockwise strategy employing suitably protected disaccharide building blocks. Carboxylic groups were introduced by selective oxidation with TEMPO (2,2,6,6-tetramethyl-1-piperidinyloxy) in the last reaction steps. Deprotection afforded target hexasaccharide 1.Key words: oligosaccharide synthesis, Streptococcus pneumoniae type 3, TEMPO oxidation.

  在开发新一代链球菌肺炎疫苗的新型糖蛋白共轭疫苗的框架下，描述了一种含有间隔物的六糖片段的合成，该片段与链球菌肺炎3型的胶囊多糖有关。通过采用适当保护的二糖单元的分块策略合成了由三个重复单元组成的六糖β-D-GlcpA-(1[Formula: see text]4)-β-D-Glcp-(1[Formula: see text]3)-β-D-GlcpA-(1[Formula: see text]4)-β-D-Glcp-(1[Formula: see text]3)-β-D-GlcpA-(1[Formula: see text]4)-β-D-Glcp-(1[Formula: see text]O-(CH₂)₃NH₂)（1）。通过TEMPO（2,2,6,6-四甲基-1-哌啶氧化物）的选择性氧化在最后的反应步骤中引入了羧基。去保护后得到目标六糖1。关键词：寡糖合成，链球菌肺炎3型，TEMPO氧化。