methyl α-D-glucuronate | 28817-88-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl α-D-glucuronate
• 英文别名: Methyl-α-D-glucopyranosiduronic saeure；Methyl-α-D-mannopyranosiduronic saeure；methyl α-D-glucopyranuronate；methyl alpha-D-glucopyranuronate；methyl (2S,3S,4S,5R,6S)-3,4,5,6-tetrahydroxyoxane-2-carboxylate
• CAS: 28817-88-1
• 化学式: C₇H₁₂O₇
• 分子量: 208.168
• InChiKey: DICCNWCUKCYGNF-QYESYBIKSA-N

物化性质

• 沸点：
  372.0±42.0 °C(Predicted)
• 密度：
  1.691±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  116
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl α-D-glucuronate 在 氢溴酸 、 四丁基硫酸氢铵 、 碳酸氢钠 、 一水合肼 、 三乙胺 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 、 溶剂黄146 为溶剂， 反应 0.33h， 生成 (2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-[(2S,3R)-3-cyclopentylmethyl-4-oxo-4-piperidin-1-yl-2-(3,4,4-trimethyl-2,5-dioxo-imidazolidin-1-ylmethyl)-butyrylaminooxy]-tetrahydro-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  The synthesis of the glucuronide adduct of Trocade™

  摘要：

  The synthetic preparation of the glucuronide adduct of Trocade(TM), a selective inhibitor of the MMP collagenase, is described. This was achieved by preparation of the protected O-glucuronsyl hydroxylamine (9) and subsequent coupling to the available carboxylic acid (7), followed by deprotection. The synthetic material was identical to authentic isolated metabolite, which confirmed that glucuronidation of Trocade(TM) occurs on the oxygen of the hydroxamic acid. (C) 2000 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(00)01556-2
• 作为产物：
  描述：

  甲醇 、 D-glucurono-6,3-lactone 在 sodium methylate 作用下， 生成 methyl α-D-glucuronate
  参考文献：
  名称：

  The synthesis of the glucuronide adduct of Trocade™

  摘要：

  The synthetic preparation of the glucuronide adduct of Trocade(TM), a selective inhibitor of the MMP collagenase, is described. This was achieved by preparation of the protected O-glucuronsyl hydroxylamine (9) and subsequent coupling to the available carboxylic acid (7), followed by deprotection. The synthetic material was identical to authentic isolated metabolite, which confirmed that glucuronidation of Trocade(TM) occurs on the oxygen of the hydroxamic acid. (C) 2000 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(00)01556-2

文献信息

• Synthesis and Antitubercular, Antimicrobial, and Hemolytic Activity of Methyl D-Glucopyranuronate and Its Simplest Derivatives
  作者：M. G. Belenok、O. V. Andreeva、B. F. Garifullin、A. S. Strobykina、M. A. Kravchenko、A. D. Voloshina、V. E. Kataev

  DOI：10.1134/s1070363217120106

  日期：2017.12

  Methyl glucuronate and some of its simplest derivatives have been synthesized, and their antitubercular, antimicrobial, and hemolytic activities have been studied. The simplest derivatives of glucuronic acid have been shown for the first time to exhibit a high antitubercular activity which is comparable with the activity of isoniazid.

  已经合成了葡萄糖醛酸甲酯及其一些最简单的衍生物，并且已经研究了它们的抗结核，抗微生物和溶血活性。葡糖醛酸的最简单的衍生物首次显示出高抗结核活性，与异烟肼的活性相当。
• Development of a Karplus equation for 3JCOCH in ester-functionalized glucopyranoses and methylglucuronate.
  作者：Sven Hackbusch、Amelia Watson、Andreas H. Franz

  DOI：10.24820/ark.5550190.p010.113

  日期：——

  Empirical Karplus equations are very useful in the conformational analysis of flexible molecules, especially with regards to carbohydrates. The C(sp2)OCH dihedral angle of ester-functionalized carbohydrates, however, is not well described by widely used Karplus equations for COCH dihedral angles, because they are based on C(sp3)OCH data. Herein, we propose a three parameter Karplus equation of the form

  经验 Karplus 方程在柔性分子的构象分析中非常有用，特别是关于碳水化合物。然而，酯官能化碳水化合物的 C(sp2)OCH 二面角并没有被广泛使用的 COCH 二面角的 Karplus 方程很好地描述，因为它们基于 C(sp3)OCH 数据。在此，我们基于 6-O-乙酰-α/ß-D-吡喃葡萄糖的量子力学计算，提出了形式为 JCOCH = 5.18 cos2(*) – 1.42 cos(*) + 1.05 的三参数 Karplus 方程. 该方程在实验确定的 JCH 值与使用 GLYCAM06 力场对一组乙酰化葡萄糖和葡萄糖醛酸甲酯进行 MD 模拟计算得出的值之间给出了令人满意的一致性。
• Fungal Glucuronoyl Esterases and Substrate Uronic Acid Recognition
  作者：Miroslava ĎURANOVÁ、Ján HIRSCH、Katarína KOLENOVÁ、Peter BIELY

  DOI：10.1271/bbb.90486

  日期：2009.11.23

  Glucuronoyl esterases are enzymes involved in microbial plant cell-wall degradation. In this study we purified and characterized two recombinant Phanerochaete chrysosporium glucuronoyl esterases, PcGE1 and PcGE2. The catalytic activity of these and previously described glucuronoyl esterases was investigated on new synthetic substrates, methyl esters of uronic acids and their glycosides, prepared by esterification with ethereal diazomethane.The data obtained indicate that the enzymes hydrolyzed efficiently not only esters of 4-O-methyl-d-glucuronic acid, but also methyl esters of d-glucuronic acid carrying a 4-nitrophenyl aglycon. Moreover, the fact that they did not recognize the 4-epimers of these compounds, the d-galacturonic acid derivatives, supports the hypothesis that these carbohydrate esterases attack ester linkages between 4-O-methyl-d-glucuronic acid of glucuronoxylan and lignin alcohols.

  葡萄糖醛酸酯酶是一种参与微生物植物细胞壁降解的酶。在这项研究中，我们纯化并鉴定了两种重组的 Phanerochaete chrysosporium 葡萄醛酰酯酶 PcGE1 和 PcGE2。获得的数据表明，这些酶不仅能有效地水解 4-O-甲基-d-葡萄糖醛酸酯，还能有效地水解带有 4-硝基苯苷元的 d-葡萄糖醛酸甲酯。此外，它们不能识别这些化合物的 4-表聚体，即 d-半乳糖醛酸衍生物，这一事实支持了这样一种假设，即这些碳水化合物酯酶能攻击葡萄糖醛酸的 4-O-甲基-d-葡萄糖醛酸与木质素醇之间的酯连接。
• Tetracyclic benzamide derivatives and methods of use thereof
  申请人：Inotek Pharmaceuticals Corporation

  公开号：US20040229895A1

  公开（公告）日：2004-11-18

  The invention relates to Tetracyclic Benzamide Derivatives; compositions comprising a Tetracyclic Benzamide Derivative; and methods for treating or preventing an inflammatory disease, a reperfusion disease, an ischemic condition, renal failure, diabetes, a diabetic complication, a vascular disease, or cancer, comprising administering to a subject in need thereof an effective amount of a Tetracyclic Benzamide Derivative.

  本发明涉及四环苯甲酰胺衍生物；包含四环苯甲酰胺衍生物的组合物；以及用于治疗或预防炎症性疾病、再灌注病、缺血症、肾衰竭、糖尿病、糖尿病并发症、血管疾病或癌症的方法，包括向需要治疗的受试者施用有效量的四环苯甲酰胺衍生物。
• Chloral hydrate detection
  申请人：Randox Laboratories Ltd.

  公开号：EP2402761A1

  公开（公告）日：2012-01-04

  The invention relates to an immunoassay method and kit for the indirect detection of chloral hydrate. The invention is underpinned by a novel immunogen that produces an antibody that is specific for the chloral hydrate metabolite trichloroethanol glucuronide. Detection and quantification of trichloroethanol glucuronide has important applications in clinical toxicology, drug facilitated crime, water testing and solvent exposure.

  本发明涉及一种间接检测水合氯醛的免疫测定方法和试剂盒。本发明以一种新型免疫原为基础，该免疫原可产生针对水合氯醛代谢物三氯乙醇葡糖醛酸的特异性抗体。三氯乙醇葡萄糖醛酸苷的检测和定量在临床毒理学、毒品犯罪、水质检测和溶剂接触等方面具有重要应用价值。