2S,4S,7R-H₄Tyr | 1385844-63-2

• 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,7R-H₄Tyr
• 英文别名: (2S)-2-amino-3-[(1S,4R)-4-hydroxycyclohex-2-en-1-yl]propanoate；(2S)-2-azaniumyl-3-[(1S,4R)-4-hydroxycyclohex-2-en-1-yl]propanoate
• CAS: 1385844-63-2
• 化学式: C₉H₁₅NO₃
• 分子量: 185.223
• InChiKey: IDAZNKKJQCQDMT-FXQIFTODSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  88
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  potassium 4S-tetrahydro-4-hydroxyphenylpyruvate 在 L-苯丙氨酸 、 L-specific transaminase ywfG 作用下， 反应 16.0h， 生成 2S,4S,7R-H₄Tyr
  参考文献：
  名称：

  在杆菌溶素途径中通过 BacABGF 将 Prephenate 转化为四氢酪氨酸期间四个立体中心的立体化学结果

  摘要：

  杆菌肽抗生素途径的前四种酶 BacABGF在通往二肽抗生素的抗辣椒素弹头的途中将 prephenate转化为四氢酪氨酸(H 4 Tyr) 非对映异构体。BACB取巴卡产物内环-Δ 4，Δ 8 -7 - [R -dihydrohydroxyphenylpyruvate（烯ħ 2 HPP），并产生3的混合物ë -和3 Ž所述的α-烯烃环外-Δ 3，Δ 5 -dihydrohydroxyphenylpyruvate（前-H 2 HPP）。然后利用 NADH 的 BacG 催化共轭还原，添加一个 pro-S氢化物相当于 C 4以产生四氢羟基苯基丙酮酸(H 4 HPP)，从 2 S -H 4 Tyr转氨基（通过 BacF）。途径酶在 D 2 O 中的培养产生了来自 BacA 的C 8处的氘掺入，然后来自 BacB 作用的C 9掺入。通过H 4 Tyr样品的1 H NMR 分析，可以确定C 4、C 8和

  DOI：

  10.1021/bi3006362

文献信息

• Stereochemical Outcome at Four Stereogenic Centers during Conversion of Prephenate to Tetrahydrotyrosine by BacABGF in the Bacilysin Pathway
  作者：Jared B. Parker、Christopher T. Walsh

  DOI：10.1021/bi3006362

  日期：2012.7.17

  NADH-utilizing BacG then catalyzes a conjugate reduction, adding a pro-S hydride equivalent to C4 to yield tetrahydrohydroxyphenylpyruvate (H4HPP), a transamination away (via BacF) from 2S-H4Tyr. Incubations of the pathway enzymes in D2O yield deuterium incorporation at C8 from BacA and then C9 from BacB action. By 1H NMR analysis of samples of H4Tyr, the stereochemistry at C4, C8, and C9 can be assigned

  杆菌肽抗生素途径的前四种酶 BacABGF在通往二肽抗生素的抗辣椒素弹头的途中将 prephenate转化为四氢酪氨酸(H 4 Tyr) 非对映异构体。BACB取巴卡产物内环-Δ 4，Δ 8 -7 - [R -dihydrohydroxyphenylpyruvate（烯ħ 2 HPP），并产生3的混合物ë -和3 Ž所述的α-烯烃环外-Δ 3，Δ 5 -dihydrohydroxyphenylpyruvate（前-H 2 HPP）。然后利用 NADH 的 BacG 催化共轭还原，添加一个 pro-S氢化物相当于 C 4以产生四氢羟基苯基丙酮酸(H 4 HPP)，从 2 S -H 4 Tyr转氨基（通过 BacF）。途径酶在 D 2 O 中的培养产生了来自 BacA 的C 8处的氘掺入，然后来自 BacB 作用的C 9掺入。通过H 4 Tyr样品的1 H NMR 分析，可以确定C 4、C 8和
• 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.