chitosan trimer | 4207-52-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: chitosan trimer
• 英文别名: chitotriose；GlcNβ1→4GlcNβ1→4GlcN；(GlcN)₃；GlcN-GlcN-GlcN；Chitooctaose Hydrochloride；(2R,3S,4R,5R,6S)-5-amino-6-[(2R,3S,4R,5R,6S)-5-amino-6-[(2R,3S,4R,5R)-5-amino-4,6-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-4-hydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-2-(hydroxymethyl)oxane-3,4-diol
• CAS: 4207-52-7
• 化学式: C₁₈H₃₅N₃O₁₃
• 分子量: 501.488
• InChiKey: RQFQJYYMBWVMQG-NLJWRWSBSA-N

物化性质

• 沸点：
  882.2±65.0 °C(Predicted)
• 密度：
  1.68±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -7.6
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  286
• 氢给体数：
  11
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  chitosan trimer 生成 chitotriose undecaacetate
  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：
• 作为产物：
  描述：

  chitotriose 在 盐酸 、 sodium tetrahydroborate 、 chitin deacetylase 作用下， 生成 chitosan trimer
  参考文献：
  名称：

  Deacetylation of chitin oligosaccharides of dp 2–4 by chitin deacetylase from Colletotrichum lindemuthianum

  摘要：

  Chitin oligosaccharides of degree of polymerization 2-4 were deacetylated by purified chitin deacetylase isolated from Colletotrichum lindemuthianum to give their corresponding breakdown products after purification by liquid chromatography. Data from FABMS analyses suggested that N, N', N '', N'''-tetraacetylchitotetraose and N, N', N ''-triacetylchitotriose were converted into fully-deacetylated corresponding chitosan oligomers. Conversely, N,N'-diacetylchitobiose [(GlcNAc)(2)] was deacetylated to give a product which showed an [M + H](+) pseudomolecular ion at m/z 383, suggesting that either of the two acetyl groups were removed. Further data from H-1 NMR analyses confirmed that the reaction product was 2-acetamido-4-O-(2-amino-2-deoxy-beta-D-glucopyranosyl)-2-deoxy-D-glucose [GlcN-GlcNAc]. The enzymatic method has three advantageous characteristics over chemical methods: (i) it does not cause unexpected degradation of the sugar chain, (ii) it is highly reproducible, and (iii) unique compounds such as GlcN-GlcNAc may be produced. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(97)00166-3

文献信息

• New glycolipids (chitooligosaccharide derivatives) possessing immunostimulating and antitumor activities
  作者：Vladimir I. Gorbach、Inna N. Krasikova、Pavel A. Luk'yanov、Yury N. Loenko、Tamara F. Solov'eva、Yury S. Ovodov、Vadim V. Deev、Alexey A. Pimenov

  DOI：10.1016/0008-6215(94)80023-5

  日期：1994.7

  New glycolipids, derived from chitooligosaccharides of dp 2-4 and containing both free and acylated amino groups, were synthesized. The structure of the key compounds (di-, tri-, and tetra-saccharides acylated with different fatty acids) were elucidated by 13C NMR spectroscopy. Only the amino group of the reducing end of the chitooligosaccharides was found to be acylated when equimolecular amounts

  合成了新的糖脂，该糖脂衍生自dp 2-4的壳寡糖，同时含有游离和酰化氨基。通过13 C NMR光谱阐明了关键化合物（被不同脂肪酸酰化的二糖，三糖和四糖）的结构。当使用等分子量的试剂时，仅发现壳寡糖的还原端的氨基被酰化。已显示获得的化合物具有低毒性以及某些免疫刺激和抗肿瘤活性。观察到免疫功能细胞诱导白细胞介素-1和肿瘤坏死因子的诱导，并增加了Erlich癌小鼠平均寿命的140-180％。
• Novel dyes and compositions, and processes for using same in analysis of protein aggregation and other applications
  申请人：Patton Wayne Forrest

  公开号：US20110130305A1

  公开（公告）日：2011-06-02

  Provided are dyes and compositions which are useful in a number of applications, such as the detection and monitoring protein aggregation, kinetic studies of protein aggregation, neurofibrillary plaques analysis, evaluation of protein formulation stability, protein thermal stability shift assay and analysis of molecular chaperone activity. These dyes and compositions are also useful as probes in nucleic acid and protein detection.

  提供了染料和组合物，这些染料和组合物在许多应用中非常有用，例如检测和监测蛋白质聚集、蛋白质聚集的动力学研究、神经原纤维样斑块分析、评估蛋白质配方稳定性、蛋白质热稳定性位移测定和分子伴侣活性分析。这些染料和组合物也可作为核酸和蛋白质检测中的探针。
• HYBRID COMPOUNDS BASED ON POLYOL(S) AND AT LEAST ONE OTHER MOLECULAR ENTITY, POLYMERIC OR NON-POLYMERIC, IN PARTICULAR OF THE POLYORGANOSILOXANE TYPE, PROCESS FOR THE PREPARATION THEREOF, AND APPLICATIONS THEREOF
  申请人：Fleury Etienne

  公开号：US20100048738A1

  公开（公告）日：2010-02-25

  The invention relates to novel hybrid compounds comprising at least one polyon entity (Po)—for example oligomer or polymer—in which at least one of the hydroxyl functions of Po is substituted by at least one entity A that can be of a variable nature, for example polymer (e.g. polyorganosiloxane-POS), hydrocarbonated or mineral. The bond Ro between the entity Po and the entity A is obtained by means of “click chemistry” and corresponds to formula (II.1) or (II.2), Z representing —CH— or —N—. A is an entity selected from the group comprising the various polyols of Po, polyorganosiloxanes (POS), polyalkylene glycols, polyamides, polyesters, polystyrenes, alkyls, alkenyls, alkynyls, aryls, and combinations thereof, in addition to mineral materials such as silica and the combinations thereof. Said hybrid components can be used as emulsifiers, especially for cosmetics.

  该发明涉及一种新型混合化合物，包括至少一个聚合物实体（Po）- 例如寡聚物或聚合物- 其中Po的至少一个羟基功能被至少一个实体A取代，该实体A可以是多种不同性质的，例如聚合物（例如聚有机硅氧烷-POS）、烃化合物或矿物质。实体Po和实体A之间的键Ro是通过“点击化学”获得的，对应于式（II.1）或（II.2），其中Z代表—CH—或—N—。实体A是从包括各种Po的多元醇、聚有机硅氧烷（POS）、聚烷基乙二醇、聚酰胺、聚酯、聚苯乙烯、烷基、烯基、炔基、芳基以及其组合物在内的群体中选择的实体，此外还包括矿物材料，如硅胶及其组合物。这些混合组分可用作乳化剂，尤其适用于化妆品。
• NOVEL COMPOSITIONS AND THERAPEUTIC METHODS
  申请人：AyuVis Research LLC

  公开号：US20170281667A1

  公开（公告）日：2017-10-05

  The present invention is directed to novel products, variants, pharmaceutically acceptable salts and prodrugs thereof, and medical use of such compounds for the treatment and/or management of sepsis, septicemia, septic shock, ocular infection, ocular inflammation, ocular angiogenesis, rheumatoid arthritis (RA), atherosclerosis, inflammatory bowel diseases (IBD), asthma, chronic obstructive pulmonary disease, fever syndromes, cachexia, psoriasis, autoimmune diseases, cardiac diseases, retinoblastoma, cancer and/or any disorder associated with inflammation, immunomodulation and microbial infection.

  本发明涉及新产品、变体、药用可接受的盐和前药，以及这些化合物的医学用途，用于治疗和/或管理败血症、败血症、脓毒性休克、眼部感染、眼部炎症、眼部血管生成、类风湿性关节炎（RA）、动脉粥样硬化、炎症性肠病（IBD）、哮喘、慢性阻塞性肺病、发热综合征、消瘦症、牛皮癣、自身免疫疾病、心脏疾病、视网膜母细胞瘤、癌症和/或任何与炎症、免疫调节和微生物感染有关的疾病。
• 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。