p-N-acryloylamidophenyl (α-D-galacopyranosyl)-(1->3)-β-D-galactopyranosyl)-(1->4)-β-D-glucopyranoside | 218617-29-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-N-acryloylamidophenyl (α-D-galacopyranosyl)-(1->3)-β-D-galactopyranosyl)-(1->4)-β-D-glucopyranoside
• 英文别名: N-[4-[(2S,3R,4R,5S,6R)-5-[(2S,3R,4S,5S,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]prop-2-enamide
• CAS: 218617-29-9
• 化学式: C₂₇H₃₉NO₁₇
• 分子量: 649.603
• InChiKey: KMHDPKOGGQVYJU-WOQNEKOKSA-N

物化性质

• 沸点：
  1021.885±65.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.654±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -4.2
• 重原子数：
  45
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  287
• 氢给体数：
  11
• 氢受体数：
  17

反应信息

• 作为产物：
  描述：

  (2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-((2-(methoxycarbonyl)phenyl)thio)tetrahydro-2H-pyran-3,4,5-triyl triacetate 在 palladium dihydroxide 吡啶 、 盐酸 、 4-二甲氨基吡啶 、 N-碘代丁二酰亚胺 、 MS 4 Angstroem 、 四丁基氟化铵 、 sodium methylate 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 61.5h， 生成 p-N-acryloylamidophenyl (α-D-galacopyranosyl)-(1->3)-β-D-galactopyranosyl)-(1->4)-β-D-glucopyranoside
  参考文献：
  名称：

  Convenient use of non-malodorous thioglycosyl donors for the assembly of multivalent globo- and isoglobosyl trisaccharides

  摘要：

  New thioglycosyl donors (o-methoxycarbonylphenyl 2,3,4,6-tetra-O-benzyl-1-thio-beta-D-galactopyranoside and its 6-O-acetyl analogue) were designed and used for the synthesis of glycoconjugate polymers carrying Gb(3) [Gal(alpha1-->4)Gal(beta1-->4)Glc] and isoGb(3) [Gal(alpha1-->3)Gal(beta1-->4)Glc] clusters as side chains. These donors scarcely evolved the unpleasant odor of thiophenols and showed a high alpha-anomeric selectivity in the galactosylation of p-nitrophenyl beta-lactoside derivatives, although in moderate yields. The derived trisaccharides were converted to multivalent carbohydrate ligands and were subjected to a biological assay with Shiga toxins. The multivalent Gb(3) ligand was highly active in inhibiting the toxicity, while the isoGb(3) ligand showed no activity, indicating that Stx-I discriminates between the carbohydrate structures. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(02)00093-9

文献信息

• Synthesis of artifical glycoconjugate polymers carrying biologically active trisaccharides with α-d-galactopyranosyl (1→3) and (1→4)-linkage
  作者：Yoshihiro Nishida、Hirofumi Dohi、Hirotaka Uzawa、Kazukiyo Kobayashi

  DOI：10.1016/s0040-4039(98)01897-8

  日期：1998.11

  Starting from p-nitrophenyl-β-lactoside, two types of neoglycoconjugate carrying either a trisaccharide segment of globotriaosyl ceramide (Gb3) or its regioisomeric Galα1,3Galβ1,4Glc were synthesized via a common intermediate. The former polymer carrying the Gb3 trisaccharide showed strong neutralization activity against Shiga-like toxin-I in the assay using human ACHN cells.

  从对硝基苯基-β-乳糖苷开始，通过共同的中间体合成了两种类型的新糖缀合物，它们携带了球果糖基神经酰胺（Gb3）的三糖片段或其区域异构体Galα1,3Galβ1,4Glc。在使用人ACHN细胞的分析中，带有Gb3三糖的前一种聚合物显示出对志贺样毒素I的强中和活性。