6-azidohexyl (β-D-glucopyranosyluronic acid)-(1→3)-(2-deoxy-2-propionamido-β-D-glucopyranosyl)-(1→4)-(β-D-glucopyranosyluronic acid)-(1→3)-(2-deoxy-2-propionamido-β-D-glucopyranosyl)-(1→4)-(β-D-glucopyranosyluronic acid)-(1→3)-2-deoxy-2-propionamido-β-D-glucopyranoside | 1448540-42-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-azidohexyl (β-D-glucopyranosyluronic acid)-(1→3)-(2-deoxy-2-propionamido-β-D-glucopyranosyl)-(1→4)-(β-D-glucopyranosyluronic acid)-(1→3)-(2-deoxy-2-propionamido-β-D-glucopyranosyl)-(1→4)-(β-D-glucopyranosyluronic acid)-(1→3)-2-deoxy-2-propionamido-β-D-glucopyranoside
• 英文别名: (2S,3S,4S,5R,6R)-6-[(2S,3R,4R,5S,6R)-2-[(2S,3S,4R,5R,6R)-6-[(2S,3R,4R,5S,6R)-2-[(2S,3S,4R,5R,6R)-6-[(2R,3R,4R,5S,6R)-2-(6-azidohexoxy)-5-hydroxy-6-(hydroxymethyl)-3-(propanoylamino)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)-3-(propanoylamino)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)-3-(propanoylamino)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
• CAS: 1448540-42-8
• 化学式: C₅₁H₈₂N₆O₃₄
• 分子量: 1323.23
• InChiKey: NFSOHTCTEDZZLK-CZOUNIDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.6
• 重原子数：
  91
• 可旋转键数：
  30
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  587
• 氢给体数：
  19
• 氢受体数：
  36

反应信息

• 作为反应物：
  描述：

  6-azidohexyl (β-D-glucopyranosyluronic acid)-(1→3)-(2-deoxy-2-propionamido-β-D-glucopyranosyl)-(1→4)-(β-D-glucopyranosyluronic acid)-(1→3)-(2-deoxy-2-propionamido-β-D-glucopyranosyl)-(1→4)-(β-D-glucopyranosyluronic acid)-(1→3)-2-deoxy-2-propionamido-β-D-glucopyranoside 在 sodium tetrahydroborate 、 palladium 10% on activated carbon 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 5.0h， 以81%的产率得到6-aminohexyl (β-D-glucopyranosyluronic acid)-(1→3)-(2-deoxy-2-propionamido-β-D-glucopyranosyl)-(1→4)-(β-D-glucopyranosyluronic acid)-(1→3)-(2-deoxy-2-propionamido-β-D-glucopyranosyl)-(1→4)-(β-D-glucopyranosyluronic acid)-(1→3)-2-deoxy-2-propionamido-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：

  在 水 、 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 以20.9 mg的产率得到6-azidohexyl (β-D-glucopyranosyluronic acid)-(1→3)-(2-deoxy-2-propionamido-β-D-glucopyranosyl)-(1→4)-(β-D-glucopyranosyluronic acid)-(1→3)-(2-deoxy-2-propionamido-β-D-glucopyranosyl)-(1→4)-(β-D-glucopyranosyluronic acid)-(1→3)-2-deoxy-2-propionamido-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