氯霉素葡糖苷酸 | 39751-33-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 氯霉素葡糖苷酸
• 英文名称: Chloramphenicol 3-O-glucuronide
• 英文别名: chloramphenicol 7-O-glucuronide；chloramphenicol glucuronide；O¹-[(2R,3R)-2-(dichloroacetyl-amino)-3-hydroxy-3-(4-nitro-phenyl)-propyl]-β-D-glucopyranuronic acid；O¹-[(2R,3R)-2-(Dichloracetyl-amino)-3-hydroxy-3-(4-nitro-phenyl)-propyl]-β-D-glucopyranuronsaeure；(2S,3S,4S,5R,6R)-6-[(2R,3R)-2-[(2,2-dichloroacetyl)amino]-3-hydroxy-3-(4-nitrophenyl)propoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• CAS: 39751-33-2
• 化学式: C₁₇H₂₀Cl₂N₂O₁₁
• 分子量: 499.259
• InChiKey: UARPTSDFEIFMJP-PEXHWNMISA-N

物化性质

• 熔点：
  170-174°C
• 沸点：
  897.7±65.0 °C(Predicted)
• 密度：
  1.71±0.1 g/cm3(Predicted)
• 溶解度：
  甲醇（微溶）、水（微溶）

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  212
• 氢给体数：
  6
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  α-D-glucuronyl fluoride 、 氯霉素 在 Escherichia coli β-glucuronidase E504G mutant 作用下， 以 aq. phosphate buffer 、 叔丁醇 为溶剂， 反应 48.0h， 生成 氯霉素葡糖苷酸
  参考文献：
  名称：

  The Escherichia coli glucuronylsynthase promoted synthesis of steroid glucuronides: improved practicality and broader scope

  摘要：

  甾体葡萄糖苷酸可以通过使用大肠杆菌葡萄糖苷酸合酶酶快速、方便地在毫克级别上制备，随后通过固相萃取进行纯化。

  DOI：

  10.1039/c4ob00984c

文献信息

• Modular approach to on-line synthesis, drug discovery and biochemical transformations using immobilized enzyme reactors
  申请人：——

  公开号：US20040053355A1

  公开（公告）日：2004-03-18

  A coupled system using extremely different enzymes with incompatible cofactors and reaction conditions has been constructed using standard liquid chromatographic formats and open tubular formats. One of the significant aspects of the present invention lies in the development of the liquid chromatographic on-line enzyme cascade. This has been illustrated by the biosynthetic pathway involving dopamine beta-hydroxylase and phenylethanolamine N-methyltransferase which encompass the synthesis of the key neurotransmitters, norepinephrine and epinephrine. The results demonstrate for the first time the immobilization of dopamine beta-hydroxylase and phenylethanolamine N-methyltransferase. The IMERs are active and can be used in a liquid chromatographic format for qualitative and quantitative determinations. The IMER-HPLC system can be used to carry out standard Michaelis-Menten enzyme kinetic studies and to quantitatively determine enzyme kinetic constants, identify specific enzyme inhibitors, provide information regarding the mode of inhibition and the inhibitor constants (K i ). A second significant aspect of the present invention lies in the ability of the immobilized enzyme reactors to be used independently or as a combination, thus providing a unique opportunity to explore the interrelationships between these enzymes, to investigate the source of diseases and to design new drug entities for identified clinical syndromes.

  利用标准液相色谱格式和开放式管式格式，构建了一个使用极其不同的酶与不相容的辅助因子和反应条件的耦合系统。本发明的一个重要方面在于开发了液相色谱在线酶级联。多巴胺 beta-羟化酶和苯乙醇胺 N-甲基转移酶参与的生物合成途径说明了这一点，这两种酶包括合成关键的神经递质--去甲肾上腺素和肾上腺素。研究结果首次证明了多巴胺 beta-羟化酶和苯乙醇胺 N-甲基转移酶的固定化。IMER 具有活性，可用于液相色谱法进行定性和定量测定。IMER-HPLC 系统可用于开展标准的 Michaelis-Menten 酶动力学研究，定量测定酶动力学常数，确定特定的酶抑制剂，提供有关抑制模式和抑制剂常数（K i ).本发明的第二个重要方面在于固定化酶反应器能够独立使用或组合使用，从而为探索这些酶之间的相互关系、研究疾病的来源以及为已确定的临床综合症设计新的药物实体提供了独特的机会。
• MODULAR APPROACH TO ON-LINE SYNTHESIS, DRUG DISCOVERY AND BIOCHEMICAL TRANSFORMATIONS USING IMMOBILIZED ENZYME REACTORS
  申请人：McGill University

  公开号：EP1290133A1

  公开（公告）日：2003-03-12
• [EN] MODULAR APPROACH TO ON-LINE SYNTHESIS, DRUG DISCOVERY AND BIOCHEMICAL TRANSFORMATIONS USING IMMOBILIZED ENZYME REACTORS<br/>[FR] APPROCHE MODULAIRE D'UNE SYNTHESE DIRECTE, DE LA DECOUVERTE DE MEDICAMENTS ET DE TRANSFORMATIONS BIOCHIMIQUES AU MOYEN DE REACTEURS ENZYMATIQUES IMMOBILISES
  申请人：UNIV MCGILL

  公开号：WO2001090298A1

  公开（公告）日：2001-11-29

  A coupled system using extremely different enzymes with incompatible cofactors and reaction conditions has been constructed using standard liquid chromatographic formats and open tubular formats. One of the significant aspects of the present invention lies in the development of the liquid chromatographic on-line enzyme cascade. This has been illustrated by the biosynthetic pathway involving dopamine beta-hydroxylase and phenylethanolamine N-methyltransferase which encompass the synthesis of the key neurotransmitters, norepinephrine and epinephrine. The results demonstrate for the first time the immobilization of dopamine beta-hydroxylase and phenylethanolamine N-methyltransferase. The IMERs are active and can be used in a liquid chromatographic format for qualitative and quantitative determinations. The IMER-HPLC system can be used to carry out standard Michaelis-Menten enzyme kinetic studies and to quantitatively determine enzyme kinetic constants, identify specific enzyme inhibitors, provide information regarding the mode of inhibition and the inhibitor constants (Ki). A second significant aspect of the present invention lies in the ability of the immobilized enzyme reactors to be used independently or as a combination, thus providing a unique opportunity to explore the interrelationships between these enzymes, to investigate the source of diseases and to design new drug entities for identified clinical syndromes.
• The Escherichia coli glucuronylsynthase promoted synthesis of steroid glucuronides: improved practicality and broader scope
  作者：Paul Ma、Nicholas Kanizaj、Shu-Ann Chan、David L. Ollis、Malcolm D. McLeod

  DOI：10.1039/c4ob00984c

  日期：——

  Steroid glucuronides can be quickly and conveniently prepared on the milligram scale using theE. coliglucuronylsynthase enzyme followed by purification with solid-phase extraction.

  甾体葡萄糖苷酸可以通过使用大肠杆菌葡萄糖苷酸合酶酶快速、方便地在毫克级别上制备，随后通过固相萃取进行纯化。