N-p-carboxyphenyl-β-D-glucosylamine | 4103-32-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-p-carboxyphenyl-β-D-glucosylamine
• 英文别名: 4-carboxy-phenyl-β-D-glucosylamine；N-4-Carboxy-phenyl-β-D-glucosylamin；4-β-D-glucopyranosylamino-benzoic acid；4-β-D-Glucopyranosylamino-benzoesaeure；4-β-D-Galactopyranosylamino-benzoesaeure；4-D-Galactit-1-ylidenamino-benzoesaeure；4-D-Glucin-1-ylidenamino-benzoesaeure；4-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]amino]benzoic acid
• CAS: 4103-32-6
• 化学式: C₁₃H₁₇NO₇
• 分子量: 299.28
• InChiKey: VXMVXDITZWJXJN-RMPHRYRLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  140
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N-p-carboxyphenyl-β-D-glucosylamine 、 乙酸酐 在 吡啶 作用下， 生成 4-(tetra-O-acetyl-β-D-glucopyranosylamino)-benzoic acid
  参考文献：
  名称：

  N-(substituted-phenyl)-D-glycopyranosylamines and their O-acetyl derivatives as potential modifiers of the formation of glycosaminoglycans

  摘要：

  D-Arabinosyl, D-ribosyl, D-glucosyl, D-galactosyl, D-mannosyl, and L-rhamnosyl N-glycosides of p-aminobenzoic acid and their O-acetyl derivatives have been synthesized, and their ability to (a) inhibit the replication of cultured B16 melanoma cells and (b) modify the synthesis of glycosaminoglycans by these neoplastic cells have been evaluated. The most cytotoxic compound of the series was N-(p-carboxyphenyl)-2,3,4-tri-O-acetyl-D-arabinopyranosylamine (8), which produced 50% inhibition of cellular proliferation at a concentration of 4 microM; a number of other compounds were relatively cytotoxic, causing 50% inhibition of cell replication at levels of 18 to 49 microM. These effects were not due to modification of glycosaminoglycan biosynthesis, since these compounds were ineffective as inhibitors or initiators of the formation of these macromolecules.

  DOI：

  10.1021/jm00363a020
• 作为产物：
  描述：

  葡萄糖 、 对氨基苯甲酸 在 乙醇 、 氯化铵 作用下， 生成 N-p-carboxyphenyl-β-D-glucosylamine
  参考文献：
  名称：

  Sannie; Lapin, Bulletin de la Societe Chimique de France, 1948, p. 892,894

  摘要：

  DOI：

文献信息

• Drug evolution: drug design at hot spots
  申请人：Konishi Yasuo

  公开号：US20060110743A1

  公开（公告）日：2006-05-25

  A new method of designing and generating compounds having an increased probability of being drugs, drug candidates, or biologically active compounds, in particular having a therapeutic utility, is disclosed. The method consists of identifying a group of bioactive compounds, preferably of diverse therapeutic uses or biological activities and built on a common building block. In this group of compounds, side chains modifying the building block are identified and used to generate a second set of compounds according to the proposed methods of hybridization”, “single substitution” or “incorporation of frequently used side chains”. If the compounds in the second set built on the same building block contain an unusually large number of drugs, preferably with diverse therapeutic uses or biological activities, they constitute a “hot spot”. A focused combinatorial library of the “hot spot” is then generated, preferably by methods of combinatorial chemistry, and compounds of this library are screened for a variety of therapeutic uses or biological activities. The method generates drugs, drug candidates, or biologically active compounds with a high probability, without requiring any prior knowledge of biological targets.

  本文揭示了一种设计和生成化合物的新方法，这些化合物具有成为药物、药物候选物或生物活性化合物的概率增加，特别是具有治疗效用。该方法包括识别一组生物活性化合物，最好是具有不同治疗用途或生物活性，并建立在共同的基础上。在这组化合物中，识别修改基础结构的侧链，并使用“杂交”、“单一替换”或“纳入常用侧链”的建议方法生成第二组化合物。如果第二组化合物建立在相同的基础结构上，包含异常数量的药物，最好是具有不同治疗用途或生物活性，它们构成一个“热点”。然后通过组合化学的方法生成一个专注的组合式库，其中包括“热点”的化合物，并对该库中的化合物进行各种治疗用途或生物活性的筛选。该方法生成的药物、药物候选物或生物活性化合物具有高概率，无需任何先前的生物靶标知识。
• N-Glucosylation in Corynebacterium glutamicum with YdhE from Bacillus lichenformis
  作者：Obed Jackson Amoah、Hue Thi Nguyen、Jae Kyung Sohng

  DOI：10.3390/molecules27113405

  日期：——

  Corynebacterium glutamicum is traditionally known as a food-grade microorganism due to its high ability to produce amino acids and its endotoxin-free recombinant protein expression factory. In recent years, studies to improve the activities of useful therapeutics and pharmaceutical compounds have led to the engineering of the therapeutically advantageous C. glutamicum cell factory system. One of the well-studied ways to improve the activities of useful compounds is glucosylation with glycosyltransferases. In this study, we successfully and efficiently glycosylated therapeutic butyl-4-aminobenzoate and other N-linked compounds in C. glutamicum using a promiscuous YdhE, which is a glycosyltransferase from Bacillus lichenformis. For efficient glucosylation, components, such as promoter, codons sequence, expression temperatures, and substrate and glucose concentrations were optimized. With glucose as the sole carbon source, we achieved a conversion rate of almost 96% of the glycosylated products in the culture medium. The glycosylated product of high concentration was successfully purified by a simple purification method, and subjected to further analysis. This is a report of the in vivo cultivation and glucosylation of N-linked compounds in C. glutamicum.

  谷氨酸棒杆菌（Corynebacterium glutamicum）因其生产氨基酸的高能力和无内毒素的重组蛋白表达工厂而被称为食品级微生物。近年来，为提高有用治疗剂和药物化合物的活性而进行的研究促使人们对具有治疗优势的谷氨酸杆菌细胞工厂系统进行工程化改造。利用糖基转移酶进行葡萄糖基化是提高有用化合物活性的一种经过深入研究的方法。在这项研究中，我们利用来自地衣芽孢杆菌（Bacillus lichenformis）的糖基转移酶 YdhE，在谷氨酸菌中成功、高效地糖基化了治疗性 4-氨基苯甲酸丁酯和其他 N-连接化合物。为了实现高效的葡萄糖基化，对启动子、密码子序列、表达温度、底物和葡萄糖浓度等成分进行了优化。在以葡萄糖为唯一碳源的情况下，培养基中糖基化产物的转化率接近 96%。通过简单的纯化方法，我们成功地纯化了高浓度的糖基化产物，并对其进行了进一步分析。这是一份关于谷氨酸棒状杆菌体内培养和 N-连接化合物糖基化的报告。
• Hanaoka, Journal of Biochemistry, 1940, vol. 31, p. 95,97
  作者：Hanaoka

  DOI：——

  日期：——
• Kato, Journal of the Agricultural Chemical Society of Japan, 1959, vol. 23, p. 551,554
  作者：Kato

  DOI：——

  日期：——
• Identification of PDZ ligands by docking-based virtual screening for the development of novel analgesic agents
  作者：Naoual Bouzidi、Hemantkumar Deokar、Alexandre Vogrig、Benjamin Boucherle、Isabelle Ripoche、Isabelle Abrunhosa-Thomas、Liam Dorr、Anne-Sophie Wattiez、Lu-Yun Lian、Philippe Marin、Christine Courteix、Sylvie Ducki

  DOI：10.1016/j.bmcl.2013.02.100

  日期：2013.5

  Disrupting the interaction between the PDZ protein, PSD-95, and its target ligands (such as the glutamate NMDA receptor or the serotonin 5-HT2A receptor) was found to reduce hyperalgesia in various models of neuropathic pain. Here, we set out to identify lead molecules which would interact with PSD-95, and hence, would potentially display analgesic activity. We describe the virtual screening of the Asinex and Cambridge databases which together contain almost one million molecules. Using three successive docking filters and visual inspection, we identified three structural classes of molecules and synthesized a potential lead compound from each class. The binding of the molecules with the PDZ domains of PSD-95 was assessed by H-1-N-15 HSQC NMR experiments. The analgesic activity of the best ligand, quinoline 2, was evaluated in vivo in a model of neuropathic pain and showed promising results. (C) 2013 Published by Elsevier Ltd.