3,4,5-trihydroxy-6-(4-methyl-2-oxo-2H-chromen-7-yloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester | 116523-82-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 3,4,5-trihydroxy-6-(4-methyl-2-oxo-2H-chromen-7-yloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester
• 英文别名: methyl 4-methylcoumarin-7-yl-β-D-glucopyranuronate
• CAS: 116523-82-1
• 化学式: C₁₇H₁₈O₉
• 分子量: 366.325
• InChiKey: GQDKDFCKXAEJCH-KSXIZUIISA-N

物化性质

• 沸点：
  599.7±50.0 °C(Predicted)
• 密度：
  1.518±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.54
• 重原子数：
  26.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  135.66
• 氢给体数：
  3.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  3,4,5-trihydroxy-6-(4-methyl-2-oxo-2H-chromen-7-yloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester 在 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.0h， 以0.068 mmol的产率得到4-甲基伞型酮-beta-D-葡糖苷酸
  参考文献：
  名称：

  Profiling of Glycosidase Activities Using Coumarin-Conjugated Glycoside Cocktails

  摘要：

  Glycosidases are a large subgroup of carbohydrate-processing enzymes that hydrolytically cleave the glycosidic bond. Glycans formed by the action of glycosidases are involved in various biological processes. Genetic abnormalities in glycosidases are associated with inherited diseases. Thus, characterization of the catalytic activities of glycosidases is of great importance. Herein, we describe a simple and rapid approach for determining glycosidase activity profiles using coumarin-conjugated glycoside cocktails.

  DOI：

  10.1021/ol062889f
• 作为产物：
  描述：

  乙酰溴-Alpha-D-葡萄糖酮酸甲基酯 在 甲醇 、 sodium hydroxide 、 苄基三乙基氯化铵 、 sodium methylate 作用下， 以 氯仿 为溶剂， 反应 6.0h， 生成 3,4,5-trihydroxy-6-(4-methyl-2-oxo-2H-chromen-7-yloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Profiling of Glycosidase Activities Using Coumarin-Conjugated Glycoside Cocktails

  摘要：

  Glycosidases are a large subgroup of carbohydrate-processing enzymes that hydrolytically cleave the glycosidic bond. Glycans formed by the action of glycosidases are involved in various biological processes. Genetic abnormalities in glycosidases are associated with inherited diseases. Thus, characterization of the catalytic activities of glycosidases is of great importance. Herein, we describe a simple and rapid approach for determining glycosidase activity profiles using coumarin-conjugated glycoside cocktails.

  DOI：

  10.1021/ol062889f

文献信息

• Practical Synthesis of the Fluorogenic Enzyme Substrate 4-Methylumbelliferyl α-l-Idopyranosiduronic Acid
  作者：Haixin Ding、Qiang Xiao、Jiameng Tian、Wenliang Ouyang、Yanling He、Qianqian Ning、Jiang Bai

  DOI：10.1055/s-0040-1708021

  日期：2020.7

  A practical and concise synthesis of 4-methylumbelliferyl α- l -idopyranosiduronic acid, a fluorogenic enzyme substrate diagnostic for α- l -iduronidase, was accomplished. It features successive radical bromination and radical reduction of easily accessible methyl 4-methyl­umbelliferyl-2,3,4-tri-O-acetyl-β- d -glucouronate in four steps with 28% overall yield.

  4-methylumbelliferyl α-l-idopyranosiduronic acid 的实用和简洁的合成已经完成，它是一种用于诊断 α-l-艾杜糖苷酸酶的荧光酶底物。它的特点是易于获得的 4-甲基伞形酮基-2,3,4-三-O-乙酰基-β-d-葡萄糖醛酸甲酯的连续自由基溴化和自由基还原分四步进行，总产率为 28%。
• [EN] AN ESTERIFICATION/SAPONIFICATION-BASED METHOD FOR LIPOSOMAL LOADING<br/>[FR] PROCÉDÉ À BASE D'ESTÉRIFICATION/SAPONIFICATION POUR CHARGEMENT LIPOSOMAL
  申请人：ACADEMIA SINICA

  公开号：WO2017120190A1

  公开（公告）日：2017-07-13

  Described herein is a method for loading a hydrophilic compound into liposomes after addition of an alkylester group to form an esterified compound. After loading, the alkylester is hydrolyzed to reform the hydrophilic compound inside the liposomes. Also described is a method for loading drugs under a glucuronide methylester form into liposomes. The glucuronide methylester form of the drug is saponified to a glucuronide form of the drug inside the liposomes for better drug retention. The glucuronide residue conjugated to drugs can be removed inside cells to regenerate the parental drug upon cell uptake, liposomal degradation and enzyme hydrolysis. In case of cancer, this method can be used to safely deliver drugs to tumors.

  本文描述了一种将亲水化合物加载到脂质体中的方法，方法是在加入烷基酯基团后形成酯化化合物。加载后，烷基酯被水解以重新在脂质体内形成亲水化合物。还描述了一种将药物以葡萄糖醛酸甲酯形式加载到脂质体中的方法。将药物的葡萄糖醛酸甲酯形式皂化为脂质体内药物的葡萄糖醛酸形式，以增强药物的保留。与药物结合的葡萄糖醛酸残基可以在细胞内去除，从而在细胞摄取、脂质体降解和酶水解过程中再生母药。在癌症情况下，这种方法可用于安全地将药物输送到肿瘤中。