5-(methoxycarbonyl)pentyl 3,4-bis-O-<β-D-galactopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranosyl>-β-D-galactopyranoside | 143545-54-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(methoxycarbonyl)pentyl 3,4-bis-O-<β-D-galactopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranosyl>-β-D-galactopyranoside
• 英文别名: 5-(Methoxycarbonyl)pentyl 3,4-di-O-{beta-D-galactopyranosyl-(1->4)-2-acetamido-2-deoxy-beta-D-glucopyranosyl}-beta-D-galactopyranoside；methyl 6-[(2R,3R,4R,5S,6R)-4,5-bis[[(2S,3R,4R,5S,6R)-3-acetamido-4-hydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy]-3-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhexanoate
• CAS: 143545-54-4
• 化学式: C₄₁H₇₀N₂O₂₈
• 分子量: 1039.0
• InChiKey: VCQBIYQIMINBCT-VQLFRDNSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -9.2
• 重原子数：
  71
• 可旋转键数：
  23
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  460
• 氢给体数：
  16
• 氢受体数：
  28

反应信息

• 作为反应物：
  描述：

  5-(methoxycarbonyl)pentyl 3,4-bis-O-<β-D-galactopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranosyl>-β-D-galactopyranoside 、 CMP-sialic acid 在 sodium cacodylate 作用下， 以 水 为溶剂， 反应 96.0h， 以71%的产率得到5-(methoxycarbonyl)pentyl 3,4-bis-O-<(ammonium 5-acetamido-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosuronate)-(2<*>3)-β-D-galactopyranosyl-(1<*>4)-2-acetamido-2-deoxy-β-D-glucopyranosyl>-β-D-galactopyranoside
  参考文献：
  名称：

  Ligand Recognition by E-Selectin: Synthesis, Inhibitory Activity and Conformational Analysis of Bivalent Sialyl Lewis x Analogs

  摘要：

  Several sialyl Lewis x dimers anchored onto a galactose template or attached to 1,4-butanediol or 1,5-pentanediol have been prepared chemoenzymatically and evaluated as inhibitors of E-selectin-mediated cell adhesion. Two monosaccharide units were simultaneously incorporated (i.e., Gal, NeuAc, Fuc) by a glycosyltransferase into a chemically synthesized core structure containing GlcNAc and Gal. Each of the galactose-anchored dimers had higher activity than the sialyl Lewis x pentasaccharide la, with the general trend being 3,6-linked > 2,3 greater than or equal to 4,6 greater than or equal to 2,6 monomer. The dimers linked to butanediol or pentanediol showed the same level of activity as the pentasaccharide monomer. Conformational analysis of these dimers with NMR indicated that each sialyl Lewis x domain of the dimers retains the same conformation as the monomer. The differences in activity of the dimers most likely derive from differences in the relative orientation and distance between the monomer domains, suggesting the importance of the linker used in the preparation of dimers.

  DOI：

  10.1021/ja00106a008
• 作为产物：
  描述：

  6-[(2R,3R,4S,5S,6R)-3-Acetoxy-6-acetoxymethyl-4,5-bis-((2S,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-hexanoic acid methyl ester 在 sodium cacodylate buffer 、 sodium methylate 、 manganese(ll) chloride 作用下， 以 甲醇 为溶剂， 反应 70.0h， 生成 5-(methoxycarbonyl)pentyl 3,4-bis-O-<β-D-galactopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranosyl>-β-D-galactopyranoside
  参考文献：
  名称：

  流感病毒的唾液酸簇抑制剂：合成、核磁共振和生物学研究。

  摘要：

  两个 αDNeuAc(26)βDGal(14)βDGlcNAc 单元是流感病毒血凝素的受体决定因素，它们已被锚定在半乳糖上，以设计能够进行双峰病毒结合的结构。To determine the optimum αDNeuAc distance for the best intramolecular binding to the hemagglutinin trimer, the attachment sites of the two αDNeuAc(26)βDGal(14)βDGlcNAc units have been systematically varied by proper choice of the galactose glycosylation sites

  DOI：

  10.1021/ja00048a004

文献信息

• Oligosaccharide inhibitors for influenza virus
  申请人：E. I. du Pont de Nemours and Company

  公开号：US05220008A1

  公开（公告）日：1993-06-15

  Heptasaccharides containing bivalent receptor determinants for the influenza virus of human isolates which inhibit binding of the virus to host cells as well as other saccharides used in preparation of the heptasaccharides are provided.

  本发明提供了含有人类分离的流感病毒双价受体决定因子的七糖，其可抑制病毒与宿主细胞结合，同时还提供了制备七糖所使用的其他糖类。