5-(methoxycarbonyl)pentyl 2-O-benzoyl-3,6-di-O-benzyl-β-D-galactopyranosyl-(1->3)-2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranoside | 1296782-14-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: 5-(methoxycarbonyl)pentyl 2-O-benzoyl-3,6-di-O-benzyl-β-D-galactopyranosyl-(1->3)-2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranoside
• 英文别名: [(2R,3R,4S,5S,6R)-2-[[(2S,4aR,6S,7R,8R,8aR)-7-azido-6-(6-methoxy-6-oxohexoxy)-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl]oxy]-5-hydroxy-4-phenylmethoxy-6-(phenylmethoxymethyl)oxan-3-yl] benzoate
• CAS: 1296782-14-3
• 化学式: C₄₇H₅₃N₃O₁₃
• 分子量: 867.95
• InChiKey: CPJANMYGQNRMIH-SLOTUNBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  63
• 可旋转键数：
  22
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  161
• 氢给体数：
  1
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  phenyl 2-O-benzoyl-3-O-benzyl-4,6-O-di-tert-butylsilylene-1-thio-β-D-galactopyranoside 、 5-(methoxycarbonyl)pentyl 2-O-benzoyl-3,6-di-O-benzyl-β-D-galactopyranosyl-(1->3)-2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 以94%的产率得到5-(methoxycarbonyl)pentyl 2,3-di-O-benzyl-4,6-O-di-tert-butylsilylene-α-D-galactopyranosyl-(1->4)-2-O-benzoyl-3,6-di-O-benzyl-β-D-galactopyranosyl-(1->3)-2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of the carbohydrate moiety from the parasite Echinococcus multilocularis and their antigenicity against human sera

  摘要：

  Stereocontrolled syntheses of biotin-labeled oligosaccharide portions with a Gal beta 1-3GalNAc core of the Em2 glycoprotein antigen obtained from the parasite Echinococcus multilocularis have been accomplished. Trisaccharide Gal beta 1-3(GlcNAc beta 1-6)GalNAc alpha 1-R (G), tetrasaccharide Gal beta 1-3(Gal beta 1-4GlcNAc beta 1-6)GalNAc alpha 1-R (I) and pentasaccharide Gal beta 1-3(Gal alpha 1-4Gal beta 1-4GlcNAc beta 1-6)GalNAc alpha 1-R (K) (R = biotinylated probe) were synthesized by block synthesis by the use of 5-(methoxycarbonyl)pentyl 2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl-(1 -> 3)-2-azido-4-O-benzyl-2-deoxy-alpha-D-galactopyranoside as a common glycosyl acceptor. Moreover, linear trisaccharide Gal alpha 1-4Gal beta 1-3GalNAc alpha 1-R (H) and branched tetrasaccharide Gal alpha 1-4Gal beta 1-3(GlcNAc beta 1-6)GalNAc alpha 1-R (1) were synthesized by stepwise wise condensation. We examined the antigenicity of these five oligosaccharides by an enzyme linked immunosorbent assay (ELISA). Our results demonstrate that biotinylated oligosaccharides H, I and K show good serodiagnostic potential to detect infections caused by the parasite E. multilocularis. Among them the linear sequence Gal alpha 1-4Gal beta 1-3GalNAc alpha 1-R in oligosaccharide (H) appears to show the highest sensitivity (95%). Moreover, our study clarified the dominant carbohydrate epitope of Em2 antigen. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.02.030
• 作为产物：
  描述：

  5-(methoxycarbonyl)pentyl 2-O-benzoyl-3,6-di-O-benzyl-4-O-chloroacetyl-β-D-galactopyranosyl-(1->3)-2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranoside 在 吡啶 、 硫脲 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以81%的产率得到5-(methoxycarbonyl)pentyl 2-O-benzoyl-3,6-di-O-benzyl-β-D-galactopyranosyl-(1->3)-2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of the carbohydrate moiety from the parasite Echinococcus multilocularis and their antigenicity against human sera

  摘要：

  Stereocontrolled syntheses of biotin-labeled oligosaccharide portions with a Gal beta 1-3GalNAc core of the Em2 glycoprotein antigen obtained from the parasite Echinococcus multilocularis have been accomplished. Trisaccharide Gal beta 1-3(GlcNAc beta 1-6)GalNAc alpha 1-R (G), tetrasaccharide Gal beta 1-3(Gal beta 1-4GlcNAc beta 1-6)GalNAc alpha 1-R (I) and pentasaccharide Gal beta 1-3(Gal alpha 1-4Gal beta 1-4GlcNAc beta 1-6)GalNAc alpha 1-R (K) (R = biotinylated probe) were synthesized by block synthesis by the use of 5-(methoxycarbonyl)pentyl 2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl-(1 -> 3)-2-azido-4-O-benzyl-2-deoxy-alpha-D-galactopyranoside as a common glycosyl acceptor. Moreover, linear trisaccharide Gal alpha 1-4Gal beta 1-3GalNAc alpha 1-R (H) and branched tetrasaccharide Gal alpha 1-4Gal beta 1-3(GlcNAc beta 1-6)GalNAc alpha 1-R (1) were synthesized by stepwise wise condensation. We examined the antigenicity of these five oligosaccharides by an enzyme linked immunosorbent assay (ELISA). Our results demonstrate that biotinylated oligosaccharides H, I and K show good serodiagnostic potential to detect infections caused by the parasite E. multilocularis. Among them the linear sequence Gal alpha 1-4Gal beta 1-3GalNAc alpha 1-R in oligosaccharide (H) appears to show the highest sensitivity (95%). Moreover, our study clarified the dominant carbohydrate epitope of Em2 antigen. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.02.030

文献信息

• Synthesis of the carbohydrate moiety from the parasite Echinococcus multilocularis and their antigenicity against human sera
  作者：Akihiko Koizumi、Kimiaki Yamano、Frank Schweizer、Tadahiro Takeda、Fumiyuki Kiuchi、Noriyasu Hada

  DOI：10.1016/j.ejmech.2011.02.030

  日期：2011.5

  Stereocontrolled syntheses of biotin-labeled oligosaccharide portions with a Gal beta 1-3GalNAc core of the Em2 glycoprotein antigen obtained from the parasite Echinococcus multilocularis have been accomplished. Trisaccharide Gal beta 1-3(GlcNAc beta 1-6)GalNAc alpha 1-R (G), tetrasaccharide Gal beta 1-3(Gal beta 1-4GlcNAc beta 1-6)GalNAc alpha 1-R (I) and pentasaccharide Gal beta 1-3(Gal alpha 1-4Gal beta 1-4GlcNAc beta 1-6)GalNAc alpha 1-R (K) (R = biotinylated probe) were synthesized by block synthesis by the use of 5-(methoxycarbonyl)pentyl 2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl-(1 -> 3)-2-azido-4-O-benzyl-2-deoxy-alpha-D-galactopyranoside as a common glycosyl acceptor. Moreover, linear trisaccharide Gal alpha 1-4Gal beta 1-3GalNAc alpha 1-R (H) and branched tetrasaccharide Gal alpha 1-4Gal beta 1-3(GlcNAc beta 1-6)GalNAc alpha 1-R (1) were synthesized by stepwise wise condensation. We examined the antigenicity of these five oligosaccharides by an enzyme linked immunosorbent assay (ELISA). Our results demonstrate that biotinylated oligosaccharides H, I and K show good serodiagnostic potential to detect infections caused by the parasite E. multilocularis. Among them the linear sequence Gal alpha 1-4Gal beta 1-3GalNAc alpha 1-R in oligosaccharide (H) appears to show the highest sensitivity (95%). Moreover, our study clarified the dominant carbohydrate epitope of Em2 antigen. (C) 2011 Elsevier Masson SAS. All rights reserved.