2408-79-9Relevant academic research and scientific papers
Binding Methylarginines and Methyllysines as Free Amino Acids: A Comparative Study of Multiple Host Classes**
Warmerdam, Zoey,Kamba, Bianca E.,Le, My-Hue,Schrader, Thomas,Isaacs, Lyle,Bayer, Peter,Hof, Fraser
, (2021/11/30)
Methylated free amino acids are an important class of targets for host-guest chemistry that have recognition properties distinct from those of methylated peptides and proteins. We present comparative binding studies for three different host classes that are each studied with multiple methylated arginines and lysines to determine fundamental structure-function relationships. The hosts studied are all anionic and include three calixarenes, two acyclic cucurbiturils, and two other cleft-like hosts, a clip and a tweezer. We determined the binding association constants for a panel of methylated amino acids using indicator displacement assays. The acyclic cucurbiturils display stronger binding to the methylated amino acids, and some unique patterns of selectivity. The two other cleft-like hosts follow two different trends, shallow host (clip) following similar trends to the calixarenes, and the other more closed host (tweezer) binding certain less-methylated amino acids stronger than their methylated counterparts. Molecular modelling sheds some light on the different preferences of the various hosts. The results identify hosts with new selectivities and with affinities in a range that could be useful for biomedical applications. The overall selectivity patterns are explained by a common framework that considers the geometry, depth of binding pockets, and functional group participation across all host classes.
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
Spontaneous N epsilon-methylation of L-lysine by formaldehyde.
Tyihak,Trezl,Rusznak
, p. 18 - 20 (2007/10/02)
It has been found that the conversion of L-lysine (1) into its corresponding N epsilon-methylated derivatives, mainly N epsilon-mono-methyl-L-lysine (5; MML), but also N epsilon, N epsilon-dimethyl-L-lysine (DML) and N epsilon, N epsilon, N epsilon-trimethyl-L-lisine (TML) takes place by treatment with formaldehyde in spontaneous reaction. The identification of N epsilon-methylated lysines was carried out by different chromatographic and spectroscopic methods. This spontaneous N epsilon-methylation of L-lysine by formaldehyde may also play an important role in living organisms.
