6-azidohexyl (β-D-glucopyranosyluronic acid)-(1→3)-(2-deoxy-2-acetamido-β-D-glucopyranosyl)-(1→4)-(β-D-glucopyranosyluronic acid)-(1→3)-(2-deoxy-2-acetamido-β-D-glucopyranosyl)-(1→4)-(β-D-glucopyranosyluronic acid)-(1→3)-2-deoxy-2-acetamido-β-D-glucopyranoside | 1448540-41-7

• 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-acetamido-β-D-glucopyranosyl)-(1→4)-(β-D-glucopyranosyluronic acid)-(1→3)-(2-deoxy-2-acetamido-β-D-glucopyranosyl)-(1→4)-(β-D-glucopyranosyluronic acid)-(1→3)-2-deoxy-2-acetamido-β-D-glucopyranoside
• 英文别名: (2S,3S,4S,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-acetamido-2-[(2S,3S,4R,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-acetamido-2-[(2S,3S,4R,5R,6R)-6-[(2R,3R,4R,5S,6R)-3-acetamido-2-(6-azidohexoxy)-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
• CAS: 1448540-41-7
• 化学式: C₄₈H₇₆N₆O₃₄
• 分子量: 1281.15
• InChiKey: NZUOFRSBNZKBAC-XDQBKBMTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -8.1
• 重原子数：
  88
• 可旋转键数：
  27
• 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-acetamido-β-D-glucopyranosyl)-(1→4)-(β-D-glucopyranosyluronic acid)-(1→3)-(2-deoxy-2-acetamido-β-D-glucopyranosyl)-(1→4)-(β-D-glucopyranosyluronic acid)-(1→3)-2-deoxy-2-acetamido-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85%的产率得到(2S,3S,4S,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-acetamido-2-[(2S,3S,4R,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-acetamido-2-[(2S,3S,4R,5R,6R)-6-[(2R,3R,4R,5S,6R)-3-acetamido-2-(6-aminohexoxy)-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)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
• 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18.7 mg的产率得到6-azidohexyl (β-D-glucopyranosyluronic acid)-(1→3)-(2-deoxy-2-acetamido-β-D-glucopyranosyl)-(1→4)-(β-D-glucopyranosyluronic acid)-(1→3)-(2-deoxy-2-acetamido-β-D-glucopyranosyl)-(1→4)-(β-D-glucopyranosyluronic acid)-(1→3)-2-deoxy-2-acetamido-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

• Programmable one cycle–one disaccharide unit modular synthesis of hyaluronan and chondroitin hybrid glycans
  作者：Shuang Li、Shuaishuai Wang、Jingyao Qu、Jingjun Han、Lin Yang、Yi Li、Lei Li、Qingwen Jia、Congcong Chen、Peixue Ling、Junqiang Fang

  DOI：10.1039/d2gc04071a

  日期：——

  play critical roles in biological processes via glycan–protein interactions. However, the structure–function relationships of GAGs and glycan-binding proteins are largely unclear due to the lack of structurally well-defined GAGs. Herein, we report a one cycle–one disaccharide unit (OCODU) enzymatic modular assembly strategy for the synthesis of hyaluronan–chondroitin hybrid glycans. With precise employment

  糖胺聚糖 (GAG)通过以下方式在生物过程中发挥关键作用聚糖-蛋白质相互作用。然而，由于缺乏结构明确的 GAG，GAG 和聚糖结合蛋白的结构-功能关系在很大程度上尚不清楚。在此，我们报告了一种用于合成透明质酸-软骨素杂化聚糖的单循环-单双糖单元 (OCODU) 酶促模块化组装策略。通过精确使用糖基转移酶，无需纯化即可在一个反应​​循环中组装二糖。使用 5 个或更少的循环即可轻松组装出从 6 聚体到 14 聚体的总共 66 个结构，而且产量很高。制造了包含这些结构的聚糖微阵列以研究聚糖-蛋白质相互作用，揭示了杂合聚糖与透明质粘附素的结合比与透明质酸的结合更强。这种合成策略为组装具有不同聚糖长度的聚合物聚糖提供了一种有效的催化方法。此外，它还促进了对功能性聚糖结合蛋白具有高结合活性的聚糖的发现。