β-N,N',N''-triacetylchitotriosylamine | 135962-89-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: β-N,N',N''-triacetylchitotriosylamine
• 英文别名: chitotriosylamine；N-[(2R,3R,4R,5S,6R)-5-[(2S,3R,4R,5S,6R)-3-acetamido-5-[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-amino-4-hydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• CAS: 135962-89-9
• 化学式: C₂₄H₄₂N₄O₁₅
• 分子量: 626.615
• InChiKey: SBCAWBIDTLQDKU-VFCSDQTKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -7.18
• 重原子数：
  43.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  301.08
• 氢给体数：
  11.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  β-N,N',N''-triacetylchitotriosylamine 在 三氟乙酸 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.25h， 生成 Fmoc-Asn(GlcNAc)3-OH
  参考文献：
  名称：

  Solid-phase synthesis of glycopeptides: synthesis of Nα-Flourenylmethoxycarbonyl L-asparagine Nβ-glycosides

  摘要：

  It was found that crude 1-glycosylamines, prepared with saturated aqueous NH4HCO3 from reducing sugars, can be coupled with Fmoc-Asp(OPfp)-O(t)Bu in N,N-dimethylformamide-water mixtures. Purification and removal of the (t)Bu group results in N-beta-glycosides of Fmoc-Asn-OH which can be used for the solid phase synthesis of glycopeptides.

  DOI：

  10.1016/0040-4039(91)80802-d
• 作为产物：
  描述：

  O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->4)-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->4)-2-acetamido-2-deoxy-D-glucopyranose 在 氨 、 碳酸氢铵 、 水 、 三氟乙酸 作用下， 以 水 为溶剂， 反应 16.0h， 生成 β-N,N',N''-triacetylchitotriosylamine
  参考文献：
  名称：

  使用钌（II）标记进行质谱分析以鉴定糖基水解酶产物。

  摘要：

  分析糖基水解酶消化的产物有助于理解酶的水解机理和底物识别。我们开发了一种新的通用技术，该技术由钌（II）复杂标记和质谱分析组成，以鉴定通过酶消化从寡糖释放的还原糖。该方法分别应用于过嗜热古细菌火球菌和and火球菌的几丁质酶和纤维素酶的酶消化。

  DOI：

  10.1271/bbb.80492

文献信息

• Synthesis of Artificial<i>N</i>-Glycopolypeptides Carrying<i>N</i>-Acetyllactosamine and Related Compounds and Their Specific Interactions with Lectins
  作者：Xiaoxiong ZENG、Takeomi MURATA、Hirokazu KAWAGISHI、Taichi USUI、Kazukiyo KOBAYASHI

  DOI：10.1271/bbb.62.1171

  日期：1998.1

  Artificial N-glycopolypeptides carrying N-acetyllactosamine (LacNAc) or related compounds were synthesized. First, sugars were converted into their corresponding β-glycosylamines with ammonium hydrogen carbonate. Then, the β-glycosylamines were condensated with the carboxyl groups of poly(L-glutamic acid). N-Glycopolypeptides with different degrees of substitution of sugars were isolated by passage through a column of Sephadex G-25. These synthetic polymers were used as model compounds in the analysis of oligosaccharide-lectin interactions. Interactions with some lectins were investigated by agar-gel double-diffusion tests and in terms of inhibition of hemagglutination. A glycopolypeptide substituted with LacNAc reacted with Erythrina cristagalli agglutinin (ECA), peanut (Arachis hypogaea) agglutinin (PNA), Ricinus communis agglutinin-120 (RCA120), wheat germ (Triticum vulgaris) agglutinin (WGA) lectins, which recognize either galactosyl or N-acetylglucosamine (GlcNAc) residues. Other synthetic glycopolymers carrying N-acetylisolactosamine, GlcNAc, N,N′-diacetylchitobiose, or N,N′,N″-triacetylchitotriose also reacted with WGA, and these last two polymers inhibited hemagglutination most. Of these five glycopolypeptides, only the one substituted with LacNAc reacted with ECA. These sugar-substituted glycopolypeptides interacted specifically with the corresponding lectins, no matter how much shorter the sugar side chains of the glycopolymers were than those of natural glycoproteins.

  合成了携带 N-乙酰半乳糖胺（LacNAc）或相关化合物的人工 N-糖多肽。首先，用碳酸氢铵将糖转化为相应的β-糖基胺。然后，β-糖基胺与聚（L-谷氨酸）的羧基缩合。通过 Sephadex G-25 柱分离出不同糖取代度的 N-糖多肽。这些合成聚合物被用作分析寡糖-凝集素相互作用的模型化合物。通过琼脂凝胶双扩散试验和血凝抑制试验研究了寡糖与一些凝集素的相互作用。以 LacNAc 取代的糖多肽与 Erythrina cristagalli 凝集素（ECA）、花生（Arachis hypogaea）凝集素（PNA）、蓖麻凝集素-120（RCA120）、小麦胚芽（Triticum vulgaris）凝集素（WGA）凝集素发生了反应，这些凝集素可识别半乳糖基或 N-乙酰葡糖胺（GlcNAc）残基。含有 N-乙酰异半乳糖胺、GlcNAc、N,N′-二乙酰壳寡糖或 N,N′,N″-三乙酰壳三糖的其他合成糖多聚物也能与 WGA 发生反应，而且后两种聚合物对血凝的抑制作用最强。在这五种糖多肽中，只有被 LacNAc 取代的糖多肽能与 ECA 反应。无论糖聚合物的糖侧链比天然糖蛋白的糖侧链短多少，这些糖取代的糖多肽都能与相应的凝集素发生特异性相互作用。