(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1→4)-(2-acetamido-3,6-di-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1→4)-2-acetamido-1,3,6-tri-O-acetyl-2-deoxy-α-D-glucopyranose | 53942-45-3

• 物质功能分类: 分析化学 - 标准品
• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1→4)-(2-acetamido-3,6-di-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1→4)-2-acetamido-1,3,6-tri-O-acetyl-2-deoxy-α-D-glucopyranose
• 英文别名: chitotriose undecaacetate；undecaacetylchitotriose；(2R,3R,4R,5S,6R)-3-Acetamido-5-(((2S,3R,4R,5S,6R)-3-acetamido-5-(((2S,3R,4R,5S,6R)-3-acetamido-4,5-diacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-4-acetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-6-(acetoxymethyl)tetrahydro-2H-pyran-2,4-d；[(2R,3S,4R,5R,6S)-5-acetamido-3-[(2S,3R,4R,5S,6R)-3-acetamido-4,5-diacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2R,3S,4R,5R,6R)-5-acetamido-4,6-diacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxy-4-acetyloxyoxan-2-yl]methyl acetate
• CAS: 53942-45-3
• 化学式: C₄₀H₅₇N₃O₂₄
• 分子量: 963.898
• InChiKey: XXMZYRVOXWCPFH-XKCDPJKDSA-N

物化性质

• 熔点：
  315 °C
• 沸点：
  1018.9±65.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)
• 溶解度：
  酸水（少许）、DMSO（少许）、乙酸乙酯（少许）、水（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  -2.8
• 重原子数：
  67
• 可旋转键数：
  26
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  344
• 氢给体数：
  3
• 氢受体数：
  24

反应信息

• 作为反应物：
  描述：

  (2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1→4)-(2-acetamido-3,6-di-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1→4)-2-acetamido-1,3,6-tri-O-acetyl-2-deoxy-α-D-glucopyranose 在 盐酸 、 溶剂黄146 作用下， 生成
  参考文献：
  名称：

  壳二糖和壳三糖噻唑啉对几丁质酶的抑制作用

  摘要：

  良好的模仿方法：发现几丁质酶水解过程中形成的恶唑啉中间体的二糖和三糖类似物是几丁质酶A的有效抑制剂。易于合成的硫代酰胺三糖具有很高的亲和力和酶促稳定性（在图2中显示了两个分子）。酶活性位点），以及基于机理的抑制方式，使得该类似物成为广谱几丁质酶抑制的有希望的候选者。

  DOI：

  10.1002/anie.200906644
• 作为产物：
  描述：

  chitosan trimer 生成 (2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1→4)-(2-acetamido-3,6-di-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1→4)-2-acetamido-1,3,6-tri-O-acetyl-2-deoxy-α-D-glucopyranose
  参考文献：
  名称：

  NAGJO, FUMIO;SAKAI, KAZUO;USUI, TAICHI;TAKAI, IZUMI;ISHIDO, YOSHIHARU, J. CARBOHYDR. CHEM., 7,(1988) N 1, 67-82

  摘要：

  DOI：

文献信息

• From Chitin to Bioactive Chitooligosaccharides and Conjugates: Access to Lipochitooligosaccharides and the TMG-chitotriomycin
  作者：Guillaume Despras、Aurélien Alix、Dominique Urban、Boris Vauzeilles、Jean-Marie Beau

  DOI：10.1002/anie.201406802

  日期：2014.10.27

  The direct and chemoselective N‐transacylation of peracetylated chitooligosaccharides (COSs), readily obtained from chitin, to give per‐N‐trifluoroacetyl derivatives offers an attractive route to size‐defined COSs and derived glycoconjugates. It involves the use of various acceptor building blocks and trifluoromethyl oxazoline dimer donors prepared with efficiency and highly reactive in 1,2‐trans glycosylation

  容易从几丁质中获得的过乙酰化壳寡糖（COSs）的直接和化学选择性N-酰基化，生成过N-三氟乙酰基衍生物，为规模确定的COS和衍生的糖缀合物提供了诱人的途径。它涉及使用各种受体构件和三氟甲基恶唑啉二聚体供体，这些供体在1,2-反式糖基化反应中高效且具有高反应性。该方法用于制备对植物具有高活性的重要共生糖脂，以及用于昆虫，真菌和细菌N-乙酰氨基葡萄糖苷酶的强效特异性抑制剂TMG-chichitriomycin 。
• Acetylated Chitosan Oligosaccharides Act as Antagonists against Glutamate-Induced PC12 Cell Death via Bcl-2/Bax Signal Pathway
  作者：Cui Hao、Lixia Gao、Yiran Zhang、Wei Wang、Guangli Yu、Huashi Guan、Lijuan Zhang、Chunxia Li

  DOI：10.3390/md13031267

  日期：——

  Chitosan oligosaccharides (COSs), depolymerized products of chitosan composed of β-(1→4) d-glucosamine units, have broad range of biological activities such as antitumour, antifungal, and antioxidant activities. In this study, peracetylated chitosan oligosaccharides (PACOs) and N-acetylated chitosan oligosaccharides (NACOs) were prepared from the COSs by chemcal modification. The structures of these monomers were identified using NMR and ESI-MS spectra. Their antagonist effects against glutamate-induced PC12 cell death were investigated. The results showed that pretreatment of PC12 cells with the PACOs markedly inhibited glutamate-induced cell death in a concentration-dependent manner. The PACOs were better glutamate antagonists compared to the COSs and the NACOs, suggesting the peracetylation is essential for the neuroprotective effects of chitosan oligosaccharides. In addition, the PACOs pretreatment significantly reduced lactate dehydrogenase release and reactive oxygen species production. It also attenuated the loss of mitochondrial membrane potential. Further studies indicated that the PACOs inhibited glutamate-induced cell death by preventing apoptosis through depressing the elevation of Bax/Bcl-2 ratio and caspase-3 activation. These results suggest that PACOs might be promising antagonists against glutamate-induced neural cell death.

  去乙酰基壳聚糖低聚糖（COSs）是由β-(1→4) d-氨基葡萄糖单元组成的壳聚糖的去聚合产物，具有广泛的生物活性，如抗肿瘤、抗真菌和抗氧化活性。在本研究中，通过化学修饰从COSs制备了全乙酰化壳聚糖低聚糖（PACOS）和N-乙酰化壳聚糖低聚糖（NACOS）。使用核磁共振（NMR）和电喷雾质谱（ESI-MS）鉴定了这些单体的结构。研究了它们对谷氨酸诱导的PC12细胞死亡的拮抗作用。结果表明，PACOS预处理PC12细胞显著抑制了谷氨酸诱导的细胞死亡，并且这种抑制作用呈浓度依赖性。与COSs和NACOS相比，PACOS表现出更好的谷氨酸拮抗作用，表明全乙酰化对壳聚糖低聚糖的神经保护作用至关重要。此外，PACOS预处理显著减少了乳酸脱氢酶的释放和活性氧的产生，并减轻了线粒体膜电位的丧失。进一步的研究表明，PACOS通过抑制Bax/Bcl-2比率升高和半胱天冬酶-3的激活来防止谷氨酸诱导的细胞凋亡。这些结果表明PACOS可能是对抗谷氨酸诱导神经细胞死亡的有前景的拮抗剂。
• The Asymmetric Dihydroxylation of Some Alkenyl 2-Acetylamino-2-deoxy-β-D-glucopyranosides: the Preparation of Optically Pure Epoxides as Putative Inhibitors of Chitinases
  作者：Jon K. Fairweather、Robert V. Stick、D. Matthew G. Tilbrook

  DOI：10.1071/c97175

  日期：——

  Various alkenyl 2-acetylamino-2-deoxy-β-D-glucopyranosides have been subjected to the Sharpless asymmetric dihydroxylation protocol to yield the corresponding diols, albeit with somewhat disappointing stereoselectivity. An alternative, more traditional approach has yielded the optically pure epoxyalkyl 2-acetylamino-2-deoxy-β-D-glucopyranosides as putative inhibitors of chitinases. As well, an epoxypropyl chito-bioside and -trioside have been prepared, each as mixtures of two diastereoisomers.

  对各种烯基 2-乙酰氨基-2-脱氧-β-D-吡喃葡萄糖苷进行了 进行 Sharpless 不对称二羟基化反应，得到了相应的二醇。 尽管其立体选择性有点令人失望。另一种 另一种更传统的方法则得到了光学纯度更高的 环氧烷基 2-乙酰氨基-2-脱氧-β-D-吡喃葡萄糖苷作为几丁质酶的假定抑制剂。 几丁质酶抑制剂。此外，还制备了环氧丙基甲壳素双糖苷和三糖苷 还制备出了环氧丙基甲壳素双糖苷和三糖苷，每种糖苷都是两种非对映异构体的混合物。
• Inaba, Toyoaki; Ohgushi, Tadayasu; Iga, Yoshiro, Chemical and pharmaceutical bulletin, 1984, vol. 32, # 4, p. 1597 - 1603
  作者：Inaba, Toyoaki、Ohgushi, Tadayasu、Iga, Yoshiro、Hasegawa, Eiichi

  DOI：——

  日期：——
• Synthesis of<scp>l</scp>-Histidine and (-)-Spinacine Chitooligosyl Amides¹
  作者：Jakob P. Ley、Martin G. Peter

  DOI：10.1080/07328309608005424

  日期：1996.1

  The synthesis of N-(2-acetamido-4-O-[2-acetamido-4-O-2-acetamido-2-deoxy- beta-D-glucopyranosyl}-2-deoxy-beta-D-glucopyranosyl]-2-deoxy-beta-D-glucopyranosyl)-L-histidine amide (3), N-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-(6S)-4,5,6,7-tetrahydroimidazo[4,5-c]pyridine-6-carboxylic amide (4) and N-(2-acetamido-4-O-[2-acetamido-2-deoxy-beta-D-glucopyranosyl]-2-deoxy-beta-D-glucopyranosyl)-(6S)-4,5,6,7-tetrahydroimidazo[4,5-c]pyridine-6-carboxamide (5) is achieved via coupling of the appropiate glycosylamines with Boc-protected L-histidine or with (6S)-4,5,6,7-tetrahydroimidazo[4,5-c]pyridine-6-carboxylic acid ((-)-spinacine), respectively, by means of EEDQ and subsequent deprotection.