methyl (2-13C)bromoacetate | 255830-59-2

• 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: methyl (2-13C)bromoacetate
• 英文别名: methyl 2-bromoacetate
• CAS: 255830-59-2
• 化学式: C₃H₅BrO₂
• 分子量: 153.964
• InChiKey: YDCHPLOFQATIDS-VQEHIDDOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  6
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-[(4-甲氧基苯基)甲氧基]乙醛 、 methyl (2-13C)bromoacetate 在 三苯基膦 、 methyloxirane 作用下， 以 二氯甲烷 为溶剂， 生成 4-(4-methoxybenzyloxy)[2-13C]but-2-enoic acid methyl ester
  参考文献：
  名称：

  Synthesis of 13C-labeled γ-hydroxybutyrates for EPR studies with 4-hydroxybutyryl-CoA dehydratase

  摘要：

  4-Hydroxybutyryl-CoA dehydratase from Clostridium aminobutyricum catalyses the reversible dehydration of its substrate 4-hydroxybutyryl-CoA (4-HB-CoA) to crotonyl CoA. The enzyme contains one [4Fe-4S](2+) cluster and one flavin adenine dinucleotide (FAD) molecule per homotetramer. Incubation of the enzyme with its substrate under equilibrium conditions followed by freezing at 77 K induced the EPR-spectrum of a neutral flavin semiquinone (g = 2.005, linewidth 2.1 mT), while at 10 K additional signals were detected. In an attempt to characterize these signals, 4-HB-CoA molecules specifically labeled with C-13 have been synthesized. This was achieved via C-13-labeled gamma-butyrolactones, which were obtained from C-13-labeled bromoacetic acids by efficient synthetic routes. Incubation of the C-13-labeled 4-hydroxybutyrate-CoA molecules with 4-hydroxybutyryi-CoA dehydratase did not lead to marked broadening of the signals.(C) 2004 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2004.09.001
• 作为产物：
  描述：

  重氮甲烷 、 溴乙酸-2-13C 以 乙醚 为溶剂， 生成 methyl (2-13C)bromoacetate
  参考文献：
  名称：

  Synthesis of 13C-labeled γ-hydroxybutyrates for EPR studies with 4-hydroxybutyryl-CoA dehydratase

  摘要：

  4-Hydroxybutyryl-CoA dehydratase from Clostridium aminobutyricum catalyses the reversible dehydration of its substrate 4-hydroxybutyryl-CoA (4-HB-CoA) to crotonyl CoA. The enzyme contains one [4Fe-4S](2+) cluster and one flavin adenine dinucleotide (FAD) molecule per homotetramer. Incubation of the enzyme with its substrate under equilibrium conditions followed by freezing at 77 K induced the EPR-spectrum of a neutral flavin semiquinone (g = 2.005, linewidth 2.1 mT), while at 10 K additional signals were detected. In an attempt to characterize these signals, 4-HB-CoA molecules specifically labeled with C-13 have been synthesized. This was achieved via C-13-labeled gamma-butyrolactones, which were obtained from C-13-labeled bromoacetic acids by efficient synthetic routes. Incubation of the C-13-labeled 4-hydroxybutyrate-CoA molecules with 4-hydroxybutyryi-CoA dehydratase did not lead to marked broadening of the signals.(C) 2004 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2004.09.001

文献信息

• Specific Isotope Enrichment of Methyl Methacrylate
  作者：Thekla M. Werkhoven、Reinier van Nispen、Johan Lugtenburg

  DOI：10.1002/(sici)1099-0690(199911)1999:11<2909::aid-ejoc2909>3.0.co;2-5

  日期：1999.11

  A synthetic scheme has been developed to prepare methyl methacrylate specifically 13C-labelled at all different positions and in any combination of positions, from simple, commercially available starting materials. According to this scheme methyl (1-13C)- and methyl (2-13C)methacrylate (1a and 1b) have been prepared with high label incorporation (99%).

  已经开发出一种合成方案，用于从简单的市售起始材料制备在所有不同位置和任何位置组合上特异性 13C 标记的甲基丙烯酸甲酯。根据该方案，(1-13C)-甲基丙烯酸甲酯和(2-13C)甲基丙烯酸甲酯(1a和1b)已制备成具有高标记掺入(99%)。
• Regioselective synthesis of 13C1-labeled 2-deoxyribonolactones
  作者：Michael P Hayes、Paul J Hatala、Brian A Sherer、Xiaohong Tong、Nilo Zanatta、Philip N Borer、James Kallmerten

  DOI：10.1016/s0040-4020(00)01148-0

  日期：2001.2

  Syntheses of the five regioselectively C-13(1)-labeled 5-O-benzyl-2-deoxyribonolactones are described. C-13(1)-Labeled deoxyribonolactones were prepared by addition of KCN to epoxides 7 and subsequent lactonization of the resulting nitriles. Integration of the independent schemes leading to the five isotopomers of 9 results in an efficient and cost effective preparation of labeled mixtures of C-13 mono-labeled deoxyribonolactones. These mixtures are the pivotal intermediates in the preparation of 'population labeled' C-13-labeled nucleoside phosphoramidites for solid-phase oligonucleotide synthesis. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Biosynthesis of virginiae butanolide A, a butyrolactone autoregulator from Streptomyces
  作者：Shohei Sakuda、Ayako Higashi、Sumiko Tanaka、Takuya Nihira、Yasuhiro Yamada

  DOI：10.1021/ja00028a037

  日期：1992.1

  Virginiae butanolide A (VB A) (3) is one of the virginiamycin-inducing factors from Streptomyces virginiae and has a unique 2,3-disubstituted butanolide skeleton which is common to other signal molecules in Streptomyces. The biosynthesis of 3 in Streptomyces antibioticus, a high producer of 3, was studied by experiments with labeled precursors. C-13 and H-2 NMR results as well as CI-MS analyses of dibenzoate samples indicated that the probable biosynthetic pathway to 3 involved coupling between a beta-keto acid derivative and a C3 unit from glycerol, such as dihydroxyacetone or a derivative.