苯丙氨酸甜菜碱 | 56755-22-7

• 物质功能分类: 天然产物 - 生物碱
• 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
• 中文名称: 苯丙氨酸甜菜碱
• 英文名称: L-N,N,N-trimethylphenylalanine
• 英文别名: phenylalanine betaine；(S)-α-Trimethylammonium-β-phenylpropionsaeure；N,N,N-trimethylphenylalanine；2-phenylalanine betaine；L-Phenylalanine betaine；(2S)-3-phenyl-2-(trimethylazaniumyl)propanoate
• CAS: 56755-22-7；129519-80-8
• 化学式: C₁₂H₁₇NO₂
• 分子量: 207.272
• InChiKey: XTFQIRIHLGODFV-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  40.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N,N-二甲基苯丙氨酸甲酯 在 硫酸 作用下， 以 硝基甲烷 为溶剂， 生成 苯丙氨酸甜菜碱
  参考文献：
  名称：

  N-季化合物-XXVIII：α-三甲基铵酸的圆二色性

  摘要：

  已经比较了α-三甲基铵羧酸的二色性吸收和α-氨基酸的二色性吸收。通过氨基酸的甲基化或通过溴酸和三甲胺之间的Menschutkin反应合成季酸。讨论了Menschutkin反应中的立体化学过程。已经确定了在合成季酸的碱性溶液中外消旋的速率。

  DOI：

  10.1016/0040-4020(73)80029-8

文献信息

• Characterization of amino acid-derived betaines by electrospray ionization tandem mass spectrometry
  作者：V. Naresh Chary、Ch. Dinesh Kumar、M. Vairamani、S. Prabhakar

  DOI：10.1002/jms.2029

  日期：2012.1

  Betaines belong to the naturally occurring osmoprotectants or compatible solutes present in a variety of plants, animals and microorganisms. In recent years, metabolomic techniques have been emerging as a fundamental tool for biologists because the constellation of these molecules and their relative proportions provide with information about the actual biochemical condition of a biological system. Therefore, identification and characterization of biologically important betaines are crucial, especially for metabolomic studies. Most of the natural betaines are derived from amino acids and related homologues. Although, theoretically, all the amino acids can be converted to corresponding betaines by simple methylation of the amine group, only a few of the amino acid-derived betaines were fully characterized in the literature. Here, we report a combined electrospray ionization tandem and high-resolution mass spectrometry study of all the betaines derived from amino acids, including the isomeric betaines. The decomposition pathway of protonated, sodiated and potassiated molecule ions that enable unambiguous characterization of the betaines including the isomeric betaines and overlapping ionic species of different betaines is distinctive. Copyright © 2012 John Wiley & Sons, Ltd.

  甜菜碱属于自然界中存在的渗透保护剂或相容性溶质，存在于各种植物、动物和微生物中。近年来，代谢组学技术已成为生物学家的基本工具，因为这些分子及其相对比例的组合提供了有关生物系统实际生化状态的信息。因此，鉴定和表征生物学上重要的甜菜碱至关重要，特别是对于代谢组学研究。大多数天然甜菜碱来源于氨基酸及其相关同源物。理论上，所有氨基酸都可以通过氨基的简单甲基化转化为相应的甜菜碱，但文献中只有少数几种氨基酸衍生甜菜碱被完全表征。在这里，我们报道了一种综合电喷雾电离串联和高分辨率质谱研究，研究了所有氨基酸衍生的甜菜碱，包括异构甜菜碱。质子化、钠化和钾化的分子离子的分解途径可以对甜菜碱进行明确表征，包括异构甜菜碱和不同甜菜碱的重叠离子物种。版权所有 © 2012 John Wiley & Sons, Ltd.
• Betaines derived from amino and hydrazino acids as phase transfer catalysts
  作者：Yuri Goldberg、Edgars Ābele、Gunārs Bremanis、Pēteris Trapenciers、Alexander Gaukhman、Juris Popelis、Artur Gomtsyan、Ivars Kalviņš、Mariya Shymanska、Edmunds Lukevics

  DOI：10.1016/s0040-4020(01)89759-3

  日期：1990.1

  Betaines derived from α-, β- and γ-amino acids (obtained by alkylation of the corresponding amino acids with O-methyl-N.N'- diisopropylisourea) as well as β-hydrazino acids (prepared by de- hydrohalogenative hydrolysis of methyl 3-(2-a1ky1-2,2-dimethy1hydrazinium) propionate halides catalyse typical phase transfer reactions (dichlorocyclopropanation of styrene, N-formylation of pyrrolidine, dehydration

  衍生自α-，β-和γ-氨基酸的甜菜碱（通过用O-甲基-N.N'-二异丙基异脲烷基化相应的氨基酸获得）以及β-肼基酸（通过甲基的脱卤化氢水解制得） 3-（2-a1ky1-2,2-dimethy1hydrazinium）丙酸酯卤化物催化典型的相转移反应（苯乙烯的二氯环丙烷化，吡咯烷的N-甲酰化，苯甲酰胺和苯乙酰胺的脱水，Williamson合成苄基丙基醚，将乙氧基羰基氮烯加成2） 3-二甲基丁烯-2。在大多数情况下，两性离子盐的活性至少类似于典型的相转移催化剂（四烷基铵盐）的活性，提出了甜菜碱1s的催化作用机理。
• N-quaternary compounds—XXVIII
  作者：M. Gacek、K. Undheim

  DOI：10.1016/0040-4020(73)80029-8

  日期：1973.1

  The dichroic absorption of α-trimethylammonium carboxylic acids has been compared with that of α-amino acids. The quaternary acids were synthesized by methylation of amino acids or by the Menschutkin reaction between bromo acids and trimethylamine. The stereochemical course in the Menschutkin reaction is discussed. Rate of racemisation in alkaline solution of the synthesized quaternary acids has been

  已经比较了α-三甲基铵羧酸的二色性吸收和α-氨基酸的二色性吸收。通过氨基酸的甲基化或通过溴酸和三甲胺之间的Menschutkin反应合成季酸。讨论了Menschutkin反应中的立体化学过程。已经确定了在合成季酸的碱性溶液中外消旋的速率。
• Ergothioneine Biosynthetic Methyltransferase EgtD Reveals the Structural Basis of Aromatic Amino Acid Betaine Biosynthesis
  作者：Allegra Vit、Laëtitia Misson、Wulf Blankenfeldt、Florian P. Seebeck

  DOI：10.1002/cbic.201402522

  日期：2015.1.2

  structures of the histidine methyltransferase EgtD. Two active‐site mutations were shown to convert this enzyme into a proficient tryptophan methyltransferase. A bioinformatics search based on these substrate specificity determinants in EgtD identified tyrosine‐ and tryptophan‐specific methyltransferases in many fungal genomes, suggesting that aromatic amino acid betaine biosynthesis is a frequent fungal

  转移酶转化：我们已经确定了组氨酸甲基转移酶EgtD的晶体结构。结果表明，有两个活性位点突变可将该酶转化为高效的色氨酸甲基转移酶。基于EgtD中这些底物特异性决定因素的生物信息学搜索在许多真菌基因组中鉴定出酪氨酸和色氨酸特异性甲基转移酶，表明芳香族氨基酸甜菜碱的生物合成是一种常见的真菌性状。
• Iyengar, R. R.; Bhattacharya, P. K., Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical, 1989, vol. 28, # 6, p. 445 - 451
  作者：Iyengar, R. R.、Bhattacharya, P. K.

  DOI：——

  日期：——