(2S,3S,4S,5R,6R)-6-[(2S,3R,4R,5S,6R)-2-[(2S,3S,4R,5R,6R)-2-carboxy-6-[(2S,3R,4R,5S,6R)-2-[(2S,3S,4R,5R,6R)-2-carboxy-6-[(2R,3R,4R,5S,6R)-2-[6-[(2-ethoxy-3,4-dioxocyclobuten-1-yl)amino]hexoxy]-5-hydroxy-6-(hydroxymethyl)-3-(propanoylamino)oxan-4-yl]oxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)-3-(propanoylamino)oxan-4-yl]oxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)-3-(propanoylamino)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid | 1448540-46-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S,4S,5R,6R)-6-[(2S,3R,4R,5S,6R)-2-[(2S,3S,4R,5R,6R)-2-carboxy-6-[(2S,3R,4R,5S,6R)-2-[(2S,3S,4R,5R,6R)-2-carboxy-6-[(2R,3R,4R,5S,6R)-2-[6-[(2-ethoxy-3,4-dioxocyclobuten-1-yl)amino]hexoxy]-5-hydroxy-6-(hydroxymethyl)-3-(propanoylamino)oxan-4-yl]oxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)-3-(propanoylamino)oxan-4-yl]oxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)-3-(propanoylamino)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
• CAS: 1448540-46-2
• 化学式: C₅₇H₈₈N₄O₃₇
• 分子量: 1421.33
• InChiKey: CCROZRYLCVCIQC-GPWYWDQBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -7.5
• 重原子数：
  98
• 可旋转键数：
  33
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  628
• 氢给体数：
  20
• 氢受体数：
  38

反应信息

• 作为产物：
  描述：

  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 、 方酸二乙酯 以 aq. phosphate buffer 、 乙醇 为溶剂， 反应 20.0h， 生成 (2S,3S,4S,5R,6R)-6-[(2S,3R,4R,5S,6R)-2-[(2S,3S,4R,5R,6R)-2-carboxy-6-[(2S,3R,4R,5S,6R)-2-[(2S,3S,4R,5R,6R)-2-carboxy-6-[(2R,3R,4R,5S,6R)-2-[6-[(2-ethoxy-3,4-dioxocyclobuten-1-yl)amino]hexoxy]-5-hydroxy-6-(hydroxymethyl)-3-(propanoylamino)oxan-4-yl]oxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)-3-(propanoylamino)oxan-4-yl]oxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)-3-(propanoylamino)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
  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