(2S,4S)-cyclohexenonyl-Ala

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S,4S)-cyclohexenonyl-Ala
• 英文别名: (2S)-2-amino-3-[(1S)-4-oxocyclohex-2-en-1-yl]propanoate；(2S)-2-azaniumyl-3-[(1S)-4-oxocyclohex-2-en-1-yl]propanoate
• 化学式: C₉H₁₃NO₃
• 分子量: 183.207
• InChiKey: XMTRSDSWKYNAPU-XPUUQOCRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  84.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  L-丙氨酸 、 (2S,4S)-cyclohexenonyl-Ala 在 Bacillus subtilis genes bacD ligase 、 5’-三磷酸腺苷 作用下， 生成 (S)-Alanyl-(S)-3-<(1S)-4-oxo-2-cyclohexen-1-yl>alanine
  参考文献：
  名称：

  Action and Timing of BacC and BacD in the Late Stages of Biosynthesis of the Dipeptide Antibiotic Bacilysin

  摘要：

  Biosynthesis of the dipeptide antibiotic bacilysin, encoded by the seven Bacillus subtilis genes bacA-G, involves diversion of flux from prephenate to the noncognate amino acid anticapsin. The anticapsin warhead is then ligated to the C-terminus of L-alanine to produce mature bacilysin. We have previously noted the formation of two diastereomers of tetrahydrotyrosine (4S- and 4R-H(4)Tyr) by tandem action of the four purified enzymes BacABGF. BacC (oxidase) and BacD (ligase) have been hypothesized to be remaining late stage enzymes in bacilysin biosynthesis. Using a combination of BacCD in vitro studies, B. subtilis deletion mutants, and isotopic feeding studies, we were able to determine that the H(4)Tyr diastereomers are actually shunt products that are not on-pathway to bacilysin biosynthesis. Dihydroanticapsin and dihydrobacilysin accumulate in extracts of a Delta bacC strain and are processed to anticapsin and then bacilysin upon addition of BacC and BacD, respectively. These results suggest the epoxide group in bacilysin is installed in an earlier step of bacilysin biosynthesis, while BacC oxidation of the C-7-hydroxyl and the subsequent BacD ligation of anticapsin to L-Ala are the penultimate and ultimate steps of bacilysin biosynthesis, respectively.

  DOI：

  10.1021/bi3016229
• 作为产物：
  描述：

  2S,4S,7R-H₄Tyr 在 Bacillus subtilis genes bacC oxidase 、 nicotinamide adenine dinucleotide 作用下， 生成 (2S,4S)-cyclohexenonyl-Ala
  参考文献：
  名称：

  Action and Timing of BacC and BacD in the Late Stages of Biosynthesis of the Dipeptide Antibiotic Bacilysin

  摘要：

  Biosynthesis of the dipeptide antibiotic bacilysin, encoded by the seven Bacillus subtilis genes bacA-G, involves diversion of flux from prephenate to the noncognate amino acid anticapsin. The anticapsin warhead is then ligated to the C-terminus of L-alanine to produce mature bacilysin. We have previously noted the formation of two diastereomers of tetrahydrotyrosine (4S- and 4R-H(4)Tyr) by tandem action of the four purified enzymes BacABGF. BacC (oxidase) and BacD (ligase) have been hypothesized to be remaining late stage enzymes in bacilysin biosynthesis. Using a combination of BacCD in vitro studies, B. subtilis deletion mutants, and isotopic feeding studies, we were able to determine that the H(4)Tyr diastereomers are actually shunt products that are not on-pathway to bacilysin biosynthesis. Dihydroanticapsin and dihydrobacilysin accumulate in extracts of a Delta bacC strain and are processed to anticapsin and then bacilysin upon addition of BacC and BacD, respectively. These results suggest the epoxide group in bacilysin is installed in an earlier step of bacilysin biosynthesis, while BacC oxidation of the C-7-hydroxyl and the subsequent BacD ligation of anticapsin to L-Ala are the penultimate and ultimate steps of bacilysin biosynthesis, respectively.

  DOI：

  10.1021/bi3016229

文献信息

• Action and Timing of BacC and BacD in the Late Stages of Biosynthesis of the Dipeptide Antibiotic Bacilysin
  作者：Jared B. Parker、Christopher T. Walsh

  DOI：10.1021/bi3016229

  日期：2013.2.5

  Biosynthesis of the dipeptide antibiotic bacilysin, encoded by the seven Bacillus subtilis genes bacA-G, involves diversion of flux from prephenate to the noncognate amino acid anticapsin. The anticapsin warhead is then ligated to the C-terminus of L-alanine to produce mature bacilysin. We have previously noted the formation of two diastereomers of tetrahydrotyrosine (4S- and 4R-H(4)Tyr) by tandem action of the four purified enzymes BacABGF. BacC (oxidase) and BacD (ligase) have been hypothesized to be remaining late stage enzymes in bacilysin biosynthesis. Using a combination of BacCD in vitro studies, B. subtilis deletion mutants, and isotopic feeding studies, we were able to determine that the H(4)Tyr diastereomers are actually shunt products that are not on-pathway to bacilysin biosynthesis. Dihydroanticapsin and dihydrobacilysin accumulate in extracts of a Delta bacC strain and are processed to anticapsin and then bacilysin upon addition of BacC and BacD, respectively. These results suggest the epoxide group in bacilysin is installed in an earlier step of bacilysin biosynthesis, while BacC oxidation of the C-7-hydroxyl and the subsequent BacD ligation of anticapsin to L-Ala are the penultimate and ultimate steps of bacilysin biosynthesis, respectively.