N-乙酰葡糖胺-6-磷酸 | 1746-32-3

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: N-乙酰葡糖胺-6-磷酸
• 英文名称: 2-N-acetylamino-2-deoxy-D-glucose-6-phosphate
• 英文别名: N-acetyl-D-glucosamine 6-phosphate；2-acetylamino-O⁶-phosphono-2-deoxy-D-glucose；2-Acetylamino-O⁶-phosphono-2-desoxy-D-glucose；N-acetylglucosamine-6-phosphate；[(2R,3S,4R,5R)-5-acetamido-2,3,4-trihydroxy-6-oxo-hexoxy]phosphonic acid；[(2R,3S,4R,5R)-5-acetamido-2,3,4-trihydroxy-6-oxohexyl] dihydrogen phosphate
• CAS: 1746-32-3
• 化学式: C₈H₁₆NO₉P
• 分子量: 301.19
• InChiKey: QDSLHWJDSQGPEE-LXGUWJNJSA-N

物化性质

• 密度：
  1.642±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -4.5
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  174
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  N-乙酰葡糖胺-6-磷酸 在 sodium tetrahydroborate 作用下， 以 水 为溶剂， 反应 1.0h， 以94 mg的产率得到[(2R,3S,4R,5S)-5-acetamido-2,3,4,6-tetrahydroxy-hexyl] dihydrogen phosphate
  参考文献：
  名称：

  Hydrophobic derivatives of 2-amino-2-deoxy-d-glucitol-6-phosphate: A new type of d-Glucosamine-6-phosphate synthase inhibitors with antifungal action

  摘要：

  Several N-acyl and ester derivatives of 2-amino-2-deoxy-D-glucitol-6-phosphate (ADGP) have been synthesised and tested as inhibitors of fungal enzymes involved in early steps of chitin biosynthesis and for antifungal activity. All the tested derivatives were found to be much poorer inhibitors of the enzyme, D-glucosamine-6-phosphate (GIcN-6-P) synthase, than the parent compound but some of them exhibited much better antifungal activity. MIC values for the investigated compounds ranged between 10 mg mL(-1), found for ADGP and 0.3 mg mL(-1) for the most active derivative, namely ADGP dimethyl ester. Increased affinity of ADGP derivatives to the artificial immobilised cell membrane was correlated with their enhanced ability to be taken up by fungal cells by free diffusion. It was found that some of the examined derivatives behaved as 'pro-drugs' and after internalisation were converted into ADGP in the cell-free extract. This conversion was relatively rapid for ADGP esters but very slow for N-acyl derivatives. Results of our studies demonstrate a possibility of design and preparation of GIcN-6-P synthase inhibitors exhibiting antifungal activity. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00049-x
• 作为产物：
  描述：

  2-deoxy-2-(4-methoxybenzylidene)amino-D-glucose 在 吡啶 、 盐酸 、 氨 、 乙酸酐 、 溶剂黄146 、 丙酮 、 铂 作用下， 生成 N-乙酰葡糖胺-6-磷酸
  参考文献：
  名称：

  Phosphoric Esters of Biological Importance. VI. The Synthesis of D-Glucosamine 6-Phosphate and N-Acetyl-D-glucosamine 6-Phosphate¹

  摘要：

  DOI：

  10.1021/ja01588a034

文献信息

• Glucosamine and Glucosamine/Anti-Inflammatory Mutual Prodrugs, Compositions, and Methods
  申请人：Capomacchia C. Anthony

  公开号：US20080020997A1

  公开（公告）日：2008-01-24

  Mutual prodrugs of glucosamine, and derivatives and analogs of glucosamine and an anti-inflammatory agent, compositions thereof, and methods for, e.g., treating disorders and conditions by administration of the compositions are provided. Topical compositions of glucosamine, and derivatives and analogs of glucosamine are also provided.

  提供了葡萄糖胺的相互藥物，以及葡萄糖胺的衍生物和類似物以及抗炎藥物，其組成物和通過給予該組成物來治療疾病和狀況的方法。同時還提供了葡萄糖胺、葡萄糖胺的衍生物和類似物的局部組成物。
• [EN] ACTIVATED N-ACETYLATED SUGARS AND OLIGOSACCHARIDES<br/>[FR] SUCRES ET OLIGOSACCHARIDES N-ACÉTYLÉS ACTIVÉS
  申请人：ZUCHEM INC

  公开号：WO2016205332A1

  公开（公告）日：2016-12-22

  The invention relates to production of uridine-5'diphospho-N-acetylglucosamine and uridine-5'diphospho-N-acetylgalactosamine. The invention further relates to the production of lacto-/V-triose II and globotetraose.

  该发明涉及尿苷-5'-二磷酸-N-乙酰葡萄糖胺和尿苷-5'-二磷酸-N-乙酰半乳糖胺的生产。该发明还涉及乳酸/ V-三糖II和球四糖的生产。
• Preparation and uses of locked-ring sugar C-glycoside derivatives
  申请人：Price Neil P.

  公开号：US20080081905A1

  公开（公告）日：2008-04-03

  “Locked-ring” C-glycoside derivatives may be prepared wherein the ring of the sugar molecule remains intact without the need for any protecting groups. These C-glycoside derivatives may be produced by first reacting an aldose reducing sugar, which may be a hexose or a pentose, with a β-diketone to form a C-glycoside ketone. The C-glycoside ketone is then reacted with a ketone reactive compound, such as a hydrazine or hydroxylamine, optionally linked to a detectable label, to form a C-glycoside derivative wherein the ketone reactive compound is conjugated to the C-glycoside at the site of the ketone. The aldose reducing sugar used in the first reaction may a simple pentose or hexose monosaccharide, or it may be optionally substituted.

  可以制备“锁定环”C-糖苷衍生物，其中糖分子的环保持完整，无需任何保护基团。这些C-糖苷衍生物可以通过首先将醛糖还原糖（可以是己糖或戊糖）与β-二酮反应以形成C-糖苷酮。然后，将C-糖苷酮与酮反应性化合物（如肼或羟胺，可选地连接到可检测的标记）反应，形成一个C-糖苷衍生物，其中酮反应性化合物与C-糖苷在酮的位置结合。在第一反应中使用的醛糖还原糖可以是简单的戊糖或己糖单糖，也可以是可选择地取代的。
• Method for the treatment and prevention of pain and inflammation with glucosamine and a cyclooxygenase-2 selective inhibitor and compositions therefor
  申请人：Pharmacia Corporation

  公开号：US20030114418A1

  公开（公告）日：2003-06-19

  A method of treating, preventing, or inhibiting pain, inflammation or inflammation-associated disorder in a subject in need of such treatment or prevention provides for treating the subject with glucosamine and a cyclooxygenase-2 selective inhibitor or prodrug thereof, wherein the amount of glucosamine and the amount of a cyclooxygenase-2 selective inhibitor or prodrug thereof together constitute a pain or inflammation suppressing treatment or prevention effective amount of the composition. Compositions and pharmaceutical compositions that contain glucosamine and a cyclooxygenase-2 selective inhibitor are also disclosed.

  一种治疗、预防或抑制需要此类治疗或预防的受试者的疼痛、炎症或与炎症相关疾病的方法包括使用氨基葡萄糖和环氧合酶-2选择性抑制剂或其前药来治疗受试者，其中氨基葡萄糖的量和环氧合酶-2选择性抑制剂或其前药的量共同构成组合物的疼痛或炎症抑制治疗或预防的有效量。还公开了含有氨基葡萄糖和环氧合酶-2选择性抑制剂的组合物和药物组合物。
• Method and compositions for the treatment and prevention of pain and inflammation with a cyclooxygenase-2 selective inhibitor and chondroitin sulfate
  申请人：Pharmacia Corporation

  公开号：US20030114416A1

  公开（公告）日：2003-06-19

  A method of treating, preventing, or inhibiting pain, inflammation or inflammation-associated disorder in a subject in need of such treatment or prevention provides for treating the subject with chondroitin sulfate and a cyclooxygenase-2 selective inhibitor, or a prodrug thereof, wherein the amount of chondroitin sulfate and the amount of a cyclooxygenase-2 selective inhibitor or a pharmaceutically acceptable salt or prodrug thereof together constitute a pain or inflammation suppressing treatment or prevention effective amount. Glucosamine can optionally be present. Compositions that contain the combination of chondroitin sulfate and cyclooxygenase-2 selective inhibitor and, optionally, the glucosamine, are disclosed, as are pharmaceutical compositions.

  一种治疗、预防或抑制疼痛、炎症或与炎症相关疾病的方法，适用于需要此类治疗或预防的受试者，包括使用软骨素硫酸和环氧合酶-2选择性抑制剂或其前药来治疗受试者，其中软骨素硫酸的数量和环氧合酶-2选择性抑制剂或其药用可接受的盐或前药的数量共同构成有效的疼痛或炎症抑制治疗或预防量。可选择添加氨基葡萄糖。公开了含有软骨素硫酸和环氧合酶-2选择性抑制剂以及可选地氨基葡萄糖的组合的组合物，以及药物组合物。