1195-94-4Relevant academic research and scientific papers
Reactions with Betaine, XIV. Synthesis of Trifluoroacetylmethylide Trifluoroacetates from Betaines
Ziegler, Erich,Wittmann, Helga
, p. 723 - 730 (1982)
The reaction of trimethylammonium acetic acid betaine (1) with trifluoroaceticanhydride (TFA) yielding trifluoroacetyl-N-methylide can be extended to triethylammonium acetic acid betaine (2), 2-pyridiniumpropionic acid betaine (9) and N,N-dimethyl-piperidinium-2-carboxylate betaine (14).Trigonelline and 3-pyridiniumpropionic acid betaine (11), however, do not react in this way.It follows that the formation of such ylides is only possible if the methylene or methine group of the betaines are flanked by ammonium and carboxylate group. - Keywords: Trifluoroaceticanhydride; Triethylammonio trifluoroacetyl methylide trifluoroacetate; 1-Pyridinio-1-trifluoroacetyl ethylide trifluoroacetate; N,N-Dimethylpiperidinio-2-trifluoroacetyl-2-ylide trifluoroacetate
Occurrence of pipecolic acid and pipecolic acid betaine (homostachydrine) in Citrus genus plants
Servillo, Luigi,Giovane, Alfonso,Balestrieri, Maria Luisa,Ferrari, Giovanna,Cautela, Domenico,Castaldo, Domenico
experimental part, p. 315 - 321 (2012/04/10)
The presence of pipecolic acid and pipecolic acid betaine, also known as homostachydrine, is herein reported for the first time in Citrus genus plants. Homostachydrine was found in fruits, seeds, and leaves of orange, lemon, and bergamot (Citrus bergamia Risso et Poit). As homostachydrine was not commercially available, as a comparative source, extracts of alfalfa leaves (Medicago sativa L.) were used, in which homostachydrine is present at high concentration. Then, the results where confirmed by comparison with an authentic standard synthesized and purified starting from pipecolic acid. The synthesized standard was characterized by a ESI-MS/MS study using a 3D ion-trap mass spectrometer. When subjected to MS/MS fragmentation in positive ion mode, homostachydrine, unlike its lower homologue proline betaine (also known as stachydrine), showed a pattern of numerous ionic fragments that allowed unambiguous identification of the compound. For the quantitation in the plant sources, high sensitivity and specificity were achieved by monitoring the transition (158→72), which is absent in the fragmentation patterns of other major osmolytes commonly used as markers for studies of abiotic stress. As for the metabolic origin of homostachydrine, the occurrence in citrus plants of pipecolic acid leads to the hypothesis that it could act as a homostachydrine precursor through direct methylation.
Characterization of amino acid-derived betaines by electrospray ionization tandem mass spectrometry
Naresh Chary,Dinesh Kumar, Ch.,Vairamani,Prabhakar
experimental part, p. 79 - 88 (2012/05/04)
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
