ethyl 3-hydroxy-3-(phenyl-d5)propanoate-1,2-13C2 | 326794-15-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: ethyl 3-hydroxy-3-(phenyl-d5)propanoate-1,2-13C2
• CAS: 326794-15-4
• 化学式: C₁₁H₁₄O₃
• 分子量: 201.169
• InChiKey: DVIBDQWVFHDBOP-TVKCGURASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.67
• 重原子数：
  14.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  ethyl 3-hydroxy-3-(phenyl-d5)propanoate-1,2-13C2 在 sodium hydroxide 作用下， 以81%的产率得到[ring-2H5,1,2-13C2]-3-hydroxy-3-phenylpropionic acid
  参考文献：
  名称：

  A Plant-like Biosynthesis of Benzoyl-CoA in the Marine Bacterium ‘Streptomyces maritimus’

  摘要：

  The first plant-like biosynthesis of benzoic acid in a prokaryote, the marine actinomycete 'Streptomyces maritimus', has been characterized. Feeding experiments with H-2- and C-13-labeled intermediates revealed that phenylalanine is metabolized to benzoyl-coenzyme A (CoA) by means of a phenylalanine ammonia lyase and subsequent beta -oxidation of cinnamoyl-CoA. Benzoyl-CoA serves as the rare starter unit of a type II polyketide synthase producing the structurally novel bacteriostatic polyketides enterocin and the wailupemycins. The results from the feeding study are consistent with the proposed biosynthetic model deduced from the cloned enterocin biosynthesis gene cluster. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00765-1
• 作为产物：
  描述：

  苯(甲)醛-2,3,4,5,6-d5 、 溴乙酸乙酯-13C2 在 chromium dichloride 、 lithium iodide 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以78%的产率得到ethyl 3-hydroxy-3-(phenyl-d5)propanoate-1,2-13C2
  参考文献：
  名称：

  A Plant-like Biosynthesis of Benzoyl-CoA in the Marine Bacterium ‘Streptomyces maritimus’

  摘要：

  The first plant-like biosynthesis of benzoic acid in a prokaryote, the marine actinomycete 'Streptomyces maritimus', has been characterized. Feeding experiments with H-2- and C-13-labeled intermediates revealed that phenylalanine is metabolized to benzoyl-coenzyme A (CoA) by means of a phenylalanine ammonia lyase and subsequent beta -oxidation of cinnamoyl-CoA. Benzoyl-CoA serves as the rare starter unit of a type II polyketide synthase producing the structurally novel bacteriostatic polyketides enterocin and the wailupemycins. The results from the feeding study are consistent with the proposed biosynthetic model deduced from the cloned enterocin biosynthesis gene cluster. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00765-1

文献信息

• A Plant-like Biosynthesis of Benzoyl-CoA in the Marine Bacterium ‘Streptomyces maritimus’
  作者：Christian Hertweck、Bradley S Moore

  DOI：10.1016/s0040-4020(00)00765-1

  日期：2000.11

  The first plant-like biosynthesis of benzoic acid in a prokaryote, the marine actinomycete 'Streptomyces maritimus', has been characterized. Feeding experiments with H-2- and C-13-labeled intermediates revealed that phenylalanine is metabolized to benzoyl-coenzyme A (CoA) by means of a phenylalanine ammonia lyase and subsequent beta -oxidation of cinnamoyl-CoA. Benzoyl-CoA serves as the rare starter unit of a type II polyketide synthase producing the structurally novel bacteriostatic polyketides enterocin and the wailupemycins. The results from the feeding study are consistent with the proposed biosynthetic model deduced from the cloned enterocin biosynthesis gene cluster. (C) 2000 Elsevier Science Ltd. All rights reserved.