5-(methoxycarbonyl)pentyl 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl-(1->3)-2-azido-4-O-benzyl-2-deoxy-α-D-galactopyranoside | 1296782-04-1

• 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: 5-(methoxycarbonyl)pentyl 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl-(1->3)-2-azido-4-O-benzyl-2-deoxy-α-D-galactopyranoside
• 英文别名: [(2R,3S,4S,5R,6R)-6-[(2R,3R,4R,5R,6S)-5-azido-2-(hydroxymethyl)-6-(6-methoxy-6-oxohexoxy)-3-phenylmethoxyoxan-4-yl]oxy-3,4,5-tribenzoyloxyoxan-2-yl]methyl benzoate
• CAS: 1296782-04-1
• 化学式: C₅₄H₅₅N₃O₁₆
• 分子量: 1002.04
• InChiKey: FBKHQAKLDYTWAZ-ZCUUFMMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  73
• 可旋转键数：
  28
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  212
• 氢给体数：
  1
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  5-(methoxycarbonyl)pentyl 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl-(1->3)-2-azido-4-O-benzyl-2-deoxy-α-D-galactopyranoside 、 3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranosyl trichloroacetimidate 在 三氟甲磺酸三甲基硅酯 作用下， 反应 1.0h， 以81%的产率得到5-(methoxycarbonyl)pentyl 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl-(1->3)-[3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl-(1->6)]-2-azido-4-O-benzyl-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：

  在 三乙基硅烷 、 三氟甲磺酸三甲基硅酯 、 camphor-10-sulfonic acid 、 二氯苯酚溴酯 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 4.08h， 生成 5-(methoxycarbonyl)pentyl 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl-(1->3)-2-azido-4-O-benzyl-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.