Partitioning of amino acids and nucleotides between water and micellar hexadecyltrimethylammonium halides

Abstract

Using quantitative gel filtration techniques partition coefficients, Kp-values, have been determined between aqueous cationic micellar hexadecyltrimethylammonium bromide, CTAB, and several biomonomer. Kp-values for 5'-adenylic acid, 5'-cytidylic acid, 5'-guanylic acid, 5'-uridylic acid and 5'-thymidylic acid are 1,400 +/- 150. Nucleotides bind to CTAB micelles effectively, but nonselectively. Conversely, the binding of tRNAs to micellar CTAB is selective. Kp-values for glutamic acid II, tyrosine and phenylalanine tRNAs (in 1.0MNaCl) are 520, 3,100 and 5,600, respectively. Kp-values for the binding of alanine, arginine, aspartic acid, glutamic acid, glycine, histidine, phenylalanine, serine, threonine and tryptophan to micellar CTAB are less than 8. Conversion of unitless Kp-values for the binding of amino acids, nucleotides and nucleosides to both anionic and cationic micelles, to K (in 1/g) values allows the comparison of clays and micelles as prebiotic concentrating media. Using correlations between surface densities of the biomonomers and their binding constants, it is shown that aqueous micelles (at pH = 8) are a better concentrating media than are clays.

Simultaneous multielement-specific detection of a novel glutathione-arsenic-selenium ion [(GS)2AsSe]? by ICP AES after micellar size- exclusion chromatography

“…Hence, one potential separation strategy could target the difference in net electrostatic charge per molecule, for example with anion-exchange chromatography. Micellar chromatography, however, has also been used successfully to separate a large variety of anions [11][12][13][14][15] and several reviews have been published since its recognition as a very useful analytical tool. [16][17][18][19][20] Because micellar chromatography could be of potential use to separate [(GS) 2 AsSe] À from GSSG, we investigated the effect of increasing amounts of hexadecyltrimethylammonium bromide (HDTAB),…”

Chromatographic Separations of Enantiomers and Underivatized Oligosaccharides

“…Chiral surfactants are another class of additives commonly used in CE for the separation of optically active compounds. Micellar and pseudo-phase liquid chromatography was first developed by Armstrong during the late 70's and early 80's (200)(201)(202)(203)(204), and its principles were easily transferred to CE (205) for chiral separations. These chiral selectors are usually low molecular weight compounds that contain a hydrophilic chiral head group and a large hydrophobic tail.…”

Thin layer chromatographic separation of pesticides, decachlorobiphenyl, and nucleosides with micellar solutions

“…In this paper we introduce a new type of mobile phase, that of solutions of surfactant aggregates or micelles. The highly selective partitioning of many solutes to micelles cannot be duplicated by any pure or mixed solvent system (1)(2)(3)(4). The fact that aqueous micellar systems can mimic certain properties of organic solvents (i.e., solubilizing nonpolar solutes) could, in some cases, eliminate the need to use potentially harmful or toxic solvents (benzene for example).…”

“…If desired, partition coefficients of substances to micelles can be measured in a variety of ways (1,3,4). It should be noted that the use of micelles in chromatographic separations is only one of a number of uses of micelles in analytical chemistry.…”