(+)-cis-(5S,6S)-1-methyl-5,6-dihydroxy-5,6-dihydro-2-pyridone | 471248-30-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (+)-cis-(5S,6S)-1-methyl-5,6-dihydroxy-5,6-dihydro-2-pyridone
• 英文别名: cis-5,6-dihydro-5,6-dihydroxy-1-methyl-2-pyridone；(2S,3S)-2,3-dihydroxy-1-methyl-2,3-dihydropyridin-6-one
• CAS: 471248-30-3
• 化学式: C₆H₉NO₃
• 分子量: 143.142
• InChiKey: FMGRBMKZKOMTOL-NJGYIYPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  60.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+)-cis-(5S,6S)-1-methyl-5,6-dihydroxy-5,6-dihydro-2-pyridone 生成 5-羟基-1-甲基-1,2-二氢吡啶-2-酮
  参考文献：
  名称：

  Dioxygenase-catalysed formation of dihydrodiol metabolites of N-methyl-2-pyridone

  摘要：

  IPTG-induced cells of a recombinant strain of Escherichia coli JM109(DE3)pDTG141 expressing naphthalene dioxygenase from Pseudomonas sp. NCIB 9816-4 oxidized specifically N-methyl-2-pyridone to give the corresponding cis5,6-dihydro-5,6-dihydroxy derivative as a major product. A small amount of the cis-3,4-dihydro-3,4-dihydroxy isomer was simultaneously formed. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00541-4
• 作为产物：
  描述：

  1-甲基-2-吡啶酮 在 E_. coli JM₁₀₉(DE₃) (pDTG₁₄₁) 、 氧气 作用下， 生成 (+)-cis-(5S,6S)-1-methyl-5,6-dihydroxy-5,6-dihydro-2-pyridone 、 (+)-cis-(3S,4S)-1-methyl-3,4-dihydroxy-3,4-dihydro-2-pyridone
  参考文献：
  名称：

  Dioxygenase-catalyzed cis-dihydroxylation of pyridine-ring systems

  摘要：

  甲苯双氧酶催化的二羟基化，在喹啉、2-氯喹啉、2-甲氧基喹啉和3-溴喹啉的碳环上，发现利用假单胞菌UV4的全细胞产生相应的对映纯的顺式-5,6-和-7,8-二氢二醇代谢产物。在2-氯喹啉、2-甲氧基喹啉和2-喹啉的3,4-键上也发现了异环顺式二氢二醇代谢产物，(+)-顺式-(3S,4S)-3,4-二羟基-3,4-二氢-2-喹啉。从含有甲苯、萘和联苯双氧酶的细菌中分离出了由1-甲基-2-吡啶酮的5,6-和3,4-键的二羟基化产生的异环顺式二氢二醇代谢产物。喹啉底物的碳环顺式二氢二醇代谢产物（苄基R）以及来自喹啉、2-喹啉和2-吡啶酮底物的异环顺二醇（烯基S）的对映过量值（ee值>98%）和绝对构型与早期模型相符，用于描述双氧酶催化的碳环芳烃顺式二羟基化。提供支持双氧酶催化的吡啶环系统顺式二羟基化的证据。关键词：双氧酶；顺式二羟基化，吡啶，2-吡啶酮，绝对构型。

  DOI：

  10.1139/v02-062

文献信息

• Dioxygenase-catalysed formation of dihydrodiol metabolites of N-methyl-2-pyridone
  作者：Ludmila Modyanova、Robert Azerad

  DOI：10.1016/s0040-4039(00)00541-4

  日期：2000.5

  IPTG-induced cells of a recombinant strain of Escherichia coli JM109(DE3)pDTG141 expressing naphthalene dioxygenase from Pseudomonas sp. NCIB 9816-4 oxidized specifically N-methyl-2-pyridone to give the corresponding cis5,6-dihydro-5,6-dihydroxy derivative as a major product. A small amount of the cis-3,4-dihydro-3,4-dihydroxy isomer was simultaneously formed. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Dioxygenase-catalyzed <i>cis</i>-dihydroxylation of pyridine-ring systems
  作者：Derek R Boyd、Narain D Sharma、Ludmila V Modyanova、Jonathan G Carroll、John F Malone、Christopher CR Allen、John TG Hamilton、David T Gibson、Rebecca E Parales、Howard Dalton

  DOI：10.1139/v02-062

  日期：2002.6.1

  Toluene dioxygenase-catalyzed dihydroxylation, in the carbocyclic rings of quinoline, 2-chloroquinoline, 2-methoxyquinoline, and 3-bromoquinoline, was found to yield the corresponding enantiopure cis-5,6- and -7,8-dihy dro diol metabolites using whole cells of Pseudomonas putida UV4. cis-Dihydroxylation at the 3,4-bond of 2-chloroquino line, 2-methoxyquinoline, and 2-quinolone was also found to yield the heterocyclic cis-dihydrodiol metabolite, (+)-cis-(3S,4S)-3,4-dihydroxy-3,4-dihydro-2-quinolone. Heterocyclic cis-dihydrodiol metabolites, resulting from dihydroxylation at the 5,6- and 3,4-bonds of 1-methyl 2-pyridone, were isolated from bacteria containing toluene, naphthalene, and biphenyl dioxygenases. The enantiomeric excess (ee) values (>98%) and the absolute configurations of the carbocyclic cis-dihydrodiol metabolites of quinoline substrates (benzylic R) and of the heterocyclic cis-diols from quinoline, 2-quinolone, and 2-pyridone substrates (allylic S) were found to be in accord with earlier models for dioxygenase-catalyzed cis-dihydroxylation of carbocyclic arenes. Evidence favouring the dioxygenase-catalyzed cis-dihydroxylation of pyridine-ring systems is presented.Key words: dioxygenases; cis-dihydroxylation, pyridines, 2-pyridones, absolute configurations.

  甲苯双氧酶催化的二羟基化，在喹啉、2-氯喹啉、2-甲氧基喹啉和3-溴喹啉的碳环上，发现利用假单胞菌UV4的全细胞产生相应的对映纯的顺式-5,6-和-7,8-二氢二醇代谢产物。在2-氯喹啉、2-甲氧基喹啉和2-喹啉的3,4-键上也发现了异环顺式二氢二醇代谢产物，(+)-顺式-(3S,4S)-3,4-二羟基-3,4-二氢-2-喹啉。从含有甲苯、萘和联苯双氧酶的细菌中分离出了由1-甲基-2-吡啶酮的5,6-和3,4-键的二羟基化产生的异环顺式二氢二醇代谢产物。喹啉底物的碳环顺式二氢二醇代谢产物（苄基R）以及来自喹啉、2-喹啉和2-吡啶酮底物的异环顺二醇（烯基S）的对映过量值（ee值>98%）和绝对构型与早期模型相符，用于描述双氧酶催化的碳环芳烃顺式二羟基化。提供支持双氧酶催化的吡啶环系统顺式二羟基化的证据。关键词：双氧酶；顺式二羟基化，吡啶，2-吡啶酮，绝对构型。