6-azidohexyl 4,6-di-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1→4)-2,4-di-O-benzoyl-6-O-levulinoyl-β-D-glucopyranosyl-(1→3)-4,6-di-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside | 1448540-35-9

• 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: 6-azidohexyl 4,6-di-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1→4)-2,4-di-O-benzoyl-6-O-levulinoyl-β-D-glucopyranosyl-(1→3)-4,6-di-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6R)-2-[[(2R,4aR,6R,7R,8R,8aS)-6-(6-azidohexoxy)-7-(1,3-dioxoisoindol-2-yl)-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl]oxy]-5-[[(2R,4aR,6S,7R,8R,8aS)-7-(1,3-dioxoisoindol-2-yl)-8-hydroxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-3-benzoyloxy-6-(4-oxopentanoyloxymethyl)oxan-4-yl] benzoate
• CAS: 1448540-35-9
• 化学式: C₇₃H₇₁N₅O₂₂
• 分子量: 1370.39
• InChiKey: DQUQIMZPICBDTA-IULHEPDOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  100
• 可旋转键数：
  28
• 环数：
  13.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  298
• 氢给体数：
  1
• 氢受体数：
  24

反应信息

• 作为反应物：
  描述：

  4-O-acetyl-2,3-di-O-benzoyl-6-O-levulinoyl-β-D-glucopyranosyl-(1→3)-4,6-di-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1→4)-2,3-di-O-benzoyl-6-O-levulinoyl-α-D-glucopyranosyl trichloroacetimidate 、 6-azidohexyl 4,6-di-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1→4)-2,4-di-O-benzoyl-6-O-levulinoyl-β-D-glucopyranosyl-(1→3)-4,6-di-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以70%的产率得到6-azidohexyl 4-O-acetyl-2,3-di-O-benzoyl-6-O-levulinoyl-β-D-glucopyranosyl-(1→3)-4,6-di-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1→4)-2,3-di-O-benzoyl-6-O-levulinoyl-β-D-glucopyranosyl-(1→3)-4,6-di-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1→4)-2,4-di-O-benzoyl-6-O-levulioyl-β-D-glucopyranosyl-(1→3)-4,6-di-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis and Immunological Characterization of Modified Hyaluronic Acid Hexasaccharide Conjugates

  摘要：

  The synthesis of a tetanus toxoid (TT)-conjugate of a hyaluronic acid (HA) hexasaccharide is described. The compound was intended for use in monitoring HA levels as a disease marker and as a potential vaccine against Group A Streptococcus (GAS) infections. We also report the synthesis of a chemically modified HA-hexasaccharide-TT conjugate in which the N-acetyl moiety of the N-acetyl-D-glucosamine residue is replaced with an N-propionyl unit in order to enhance immunogenicity. The oligosaccharides are synthesized in a convergent manner. The TT-conjugate syntheses rely on the reaction of the amines on the 6-aminohexyl aglycon of the hexasaccharides with diethyl squarate to give the monoethyl squarate adducts. Subsequent reactions with lysine epsilon-amino groups on TT then give the glycoconjugates containing an average of 8 hexasaccharide haptens per TT molecule. Immunological studies in mice show very similar antibody responses with both conjugates, suggesting that the N-acetyl groups of the glucosaminyl residues of the HA-hexasaccharide are not a critical part of the epitope recognized by the anti-HA polyclonal immune response. Furthermore, it would appear that the N-acyl moieties are not in close contact with the amino acid residues of the antibody combining sites.

  DOI：

  10.1021/jo4012442
• 作为产物：
  描述：

  6-azidohexyl 4,6-di-O-benzylidene-3-O-chloroacetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1→4)-2,4-di-Obenzoyl-6-O-levulinoyl-β-D-glucopyranosyl-(1→3)-4,6-di-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside 在 2,4-二甲基吡啶 、 硫脲 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 6.0h， 以78%的产率得到6-azidohexyl 4,6-di-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1→4)-2,4-di-O-benzoyl-6-O-levulinoyl-β-D-glucopyranosyl-(1→3)-4,6-di-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis and Immunological Characterization of Modified Hyaluronic Acid Hexasaccharide Conjugates

  摘要：

  The synthesis of a tetanus toxoid (TT)-conjugate of a hyaluronic acid (HA) hexasaccharide is described. The compound was intended for use in monitoring HA levels as a disease marker and as a potential vaccine against Group A Streptococcus (GAS) infections. We also report the synthesis of a chemically modified HA-hexasaccharide-TT conjugate in which the N-acetyl moiety of the N-acetyl-D-glucosamine residue is replaced with an N-propionyl unit in order to enhance immunogenicity. The oligosaccharides are synthesized in a convergent manner. The TT-conjugate syntheses rely on the reaction of the amines on the 6-aminohexyl aglycon of the hexasaccharides with diethyl squarate to give the monoethyl squarate adducts. Subsequent reactions with lysine epsilon-amino groups on TT then give the glycoconjugates containing an average of 8 hexasaccharide haptens per TT molecule. Immunological studies in mice show very similar antibody responses with both conjugates, suggesting that the N-acetyl groups of the glucosaminyl residues of the HA-hexasaccharide are not a critical part of the epitope recognized by the anti-HA polyclonal immune response. Furthermore, it would appear that the N-acyl moieties are not in close contact with the amino acid residues of the antibody combining sites.

  DOI：

  10.1021/jo4012442

文献信息

• Synthesis and Immunological Characterization of Modified Hyaluronic Acid Hexasaccharide Conjugates
  作者：Guofeng Gu、Pal John Pal Adabala、Monica G. Szczepina、Silvia Borrelli、B. Mario Pinto

  DOI：10.1021/jo4012442

  日期：2013.8.16

  The synthesis of a tetanus toxoid (TT)-conjugate of a hyaluronic acid (HA) hexasaccharide is described. The compound was intended for use in monitoring HA levels as a disease marker and as a potential vaccine against Group A Streptococcus (GAS) infections. We also report the synthesis of a chemically modified HA-hexasaccharide-TT conjugate in which the N-acetyl moiety of the N-acetyl-D-glucosamine residue is replaced with an N-propionyl unit in order to enhance immunogenicity. The oligosaccharides are synthesized in a convergent manner. The TT-conjugate syntheses rely on the reaction of the amines on the 6-aminohexyl aglycon of the hexasaccharides with diethyl squarate to give the monoethyl squarate adducts. Subsequent reactions with lysine epsilon-amino groups on TT then give the glycoconjugates containing an average of 8 hexasaccharide haptens per TT molecule. Immunological studies in mice show very similar antibody responses with both conjugates, suggesting that the N-acetyl groups of the glucosaminyl residues of the HA-hexasaccharide are not a critical part of the epitope recognized by the anti-HA polyclonal immune response. Furthermore, it would appear that the N-acyl moieties are not in close contact with the amino acid residues of the antibody combining sites.