β-N-acetyllactosaminylamine | 163559-38-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: β-N-acetyllactosaminylamine
• 英文别名: β-N-acetyllactosylamine；N-[(2R,3R,4R,5S,6R)-2-amino-4-hydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-3-yl]acetamide
• CAS: 163559-38-4
• 化学式: C₁₄H₂₆N₂O₁₀
• 分子量: 382.368
• InChiKey: HQFIHILEYCOUEL-LODBTCKLSA-N

物化性质

• 沸点：
  776.4±60.0 °C(Predicted)
• 密度：
  1.59±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -5.29
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  204.19
• 氢给体数：
  8.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  β-N-acetyllactosaminylamine 在 三氟乙酸 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.05h， 生成 2-acetamido-2-deoxy-4-O-(β-D-galactopyranosyl)-N-glycyl-β-D-glucopyranosylamine
  参考文献：
  名称：

  Synthesis of N-glycyl-β-glycopyranosylamines, derivatives of main human secreted oligosaccharide core structures

  摘要：

  通过在氨水存在下，将氨基甲酸铵与对应于人乳和尿液低聚糖核心结构的双糖、四糖和六糖在甲醇水溶液中反应，合成了β-吡喃葡糖苷胺。随后，这些β-吡喃葡糖苷胺与N-Boc-甘氨酸N-羟基琥珀酰亚胺酯进行N-酰化反应，并除去Boc保护基，以高达60%的产率得到了相应的低聚糖的N-甘氨酰基-β-吡喃葡糖苷胺。

  DOI：

  10.1007/s11172-019-2401-y
• 作为产物：
  描述：

  N-乙酰-D-乳糖胺 在 ammonium hydroxide 、 氨基甲酸铵 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 β-N-acetyllactosaminylamine
  参考文献：
  名称：

  Synthesis of N-glycyl-β-glycopyranosylamines, derivatives of main human secreted oligosaccharide core structures

  摘要：

  通过在氨水存在下，将氨基甲酸铵与对应于人乳和尿液低聚糖核心结构的双糖、四糖和六糖在甲醇水溶液中反应，合成了β-吡喃葡糖苷胺。随后，这些β-吡喃葡糖苷胺与N-Boc-甘氨酸N-羟基琥珀酰亚胺酯进行N-酰化反应，并除去Boc保护基，以高达60%的产率得到了相应的低聚糖的N-甘氨酰基-β-吡喃葡糖苷胺。

  DOI：

  10.1007/s11172-019-2401-y

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。
• A Fluorometric Assay for Glycosyltransferase Activities Using Sugars Aminated and Tagged with 7-Hydroxycoumarin-3-carboxylic Acid as Substrates and High Performance Liquid Chromatography.
  作者：Koji HIGAI、Daisuke MASUDA、Yukinari MATSUZAWA、Tamae SATOH、Kojiro MATSUMOTO

  DOI：10.1248/bpb.22.333

  日期：——

  We developed a novel fluorometric assay method for the measurement of glycosyltransferase activities using mono- and di-saccharides aminated and tagged with 7-hydroxycoumarin-3-carboxylic acid (coumarin) as substrates, N-acetylglucosamine (GlcNAc)-coumarin for β1, 4-galactosyltransferase from boivne milk and Galβ1-4GlcNAc-coumarin for α2, 3- and α2, 6-sialyltransferases from rat liver. Using Galβ1-3GlcNAc and Galβ1-4Glc-NAc-coumarin, α1, 3/4- and α1, 3-fucosyltransferase activities were also determined, respectively. These enzymatic products liberated by the reactions of glycosyltransferases in the presence of sugar nucleotides, were separated by a normal phase or an ion-pair reversed phase HPLC with an isocratic elution and fluorescence detection. We applied this assay method to determine the glycosyltransferase activities in 8 kinds of human tumor cell lines, including the cell lines derived from hepatocytes (HuH-7, HepG2), colonic cells (Colo205, HT-29), myelocytes (HL-60, U-937), B-lymphocytes (Daude) and T-lymphocytes (Jurkat). This assay method is accurate and easy compared with other isotopic and non-isotopic assay methods, and is sensitive enough to measure glycosyltransferase activities in cell homogenates.

  我们开发了一种新的荧光测定法，以氨基化并标记有 7-羟基香豆素-3-羧酸（香豆素）的单糖和二糖为底物，测定糖基转移酶的活性、N-乙酰葡糖胺（GlcNAc）-香豆素用于牛乳中的β1，4-半乳糖基转移酶，Galβ1-4GlcNAc-香豆素用于大鼠肝脏中的α2，3-和α2，6-半乳糖基转移酶。利用 Galβ1-3GlcNAc 和 Galβ1-4Glc-NAc-coumarin 还分别测定了 α1, 3/4- 和 α1, 3-岩藻糖基转移酶的活性。糖基转移酶在糖核苷酸存在的情况下反应生成的这些酶产物通过正相或离子对反相高效液相色谱分离，采用等度洗脱和荧光检测。我们应用这种检测方法测定了 8 种人类肿瘤细胞系的糖基转移酶活性，包括肝细胞（HuH-7、HepG2）、结肠细胞（Colo205、HT-29）、骨髓细胞（HL-60、U-937）、B 淋巴细胞（Daude）和 T 淋巴细胞（Jurkat）。与其他同位素和非同位素测定方法相比，这种测定方法准确、简便，而且灵敏度高，足以测定细胞匀浆中的糖基转移酶活性。
• Synthesis of multivalent sialyllactosamine-carrying glyco-nanoparticles with high affinity to the human influenza virus hemagglutinin
  作者：Makoto Ogata、Seiichiro Umemura、Naohiro Sugiyama、Natsuki Kuwano、Ami Koizumi、Tadakazu Sawada、Michiyo Yanase、Takeshi Takaha、Jun-ichi Kadokawa、Taichi Usui

  DOI：10.1016/j.carbpol.2016.07.083

  日期：2016.11

  interactions of the sialoglyco-nanoparticles (Neu5Acα2,6LacNAc-GlcA-HBCDs) with human influenza virus strain A/Beijing/262/95 (H1N1) were investigated using a hemagglutination inhibition assay. The sialoglyco-nanoparticle, in which the number of sialic acid substitution is 30, acted as a powerful inhibitor of virus binding activity. We show that both distance and multiplicity of effective ligand-virus formation

  以高支链的α-葡萄糖醛酸连接的环状糊精（GlcA-HBCD）为骨架，有效地合成了一系列多价唾液酸共轭纳米颗粒。可以将具有不同取代度的唾液酸糖苷部分掺入到预制的纳米颗粒上。这些在水溶液中高度可溶的合成颗粒显示出具有直径约15nm的球形纳米结构。使用血凝抑制试验研究了唾液酸纳米颗粒（Neu5Acα2,6LacNAc-GlcA-HBCD）与人流感病毒A / Beijing / 262/95（H1N1）的相互作用。唾液酸取代数目为30的唾液酸纳米颗粒，起着强大的病毒结合活性抑制剂的作用。我们显示有效的配体病毒形成的距离和多样性在增强病毒抑制中起重要作用。我们的结果表明，GlcA-HBCD主链可以用作新型球形纳米簇材料，用于制备各种糖纳米颗粒以促进分子识别。