Chiral discrimination of α‐amino acids by DNA tetranucleotides under electrospray ionization conditions

Abstract

A set of DNA tetranucleotides, which are 3'- or 5'-end extended versions of GCA, was used as chiral selectors for the discrimination of enantiomers of alpha-amino acids. The [X+Y-2H](2-) ions of the 1:1 complexes were generated by electrospraying a mixture of tetranucleotide (X) and amino acid (Y) solution. Chiral discrimination was achieved by studying the collision-induced dissociation spectra of the [X+Y-2H](2-) ion and the ratio of relative abundance of precursor ion to that of the product ion was used to measure the extent of discrimination. Among the tetranucleotides used, GCAA and GGCA exhibited better discrimination, in which GCAA showed D-selectivity and GGCA showed L-selectivity for the studied amino acids. In addition, binding constants were measured for the 1:1 complexes of phenylalanine enantiomers with GCAA and GGCA. Ltd.

Analysis of stereoisomers of chiral drug by mass spectrometry

“…It was found that the derivatives of 2 melamine perform the best chiral distinction effect, whose CR value is far from 1. Vairamani et al 44,45 used the nucleotide as ligand to differentiate amino acids. In addition to protonated ternary complexes, metal ion centered ternary complexes are also available to CR method.…”

Chirality effects in gas-phase spectroscopy and photophysics of molecular and ionic complexes: contribution of low and room temperature studies

“…Briefly, the diastereomeric ion of interest is first isolated in the ion trap in a first MS step. The selected precursor is then activated by absorption of IR or UV photons or CID [35,49,[95][96][97][98]. The dissociation efficiency is described in terms of fragmentation yield Q F…”

Homochiral vs. heterochiral sodium core dimers of tartaric acid esters: A mass spectrometry and vibrational spectroscopy study

“…These experiments rest on the comparison between the collision-induced dissociation efficiency of diastereomer complexes, both in a single-collision regime 11 or in a multiple collision regime under ion trap conditions. [12][13][14][15][16][17] Tandem mass spectrometry experiments based on the kinetic method allow quantifying chirality effects. [18][19] The enantioselectivity in the dissociation is related to different binding energies or different barriers to dissociation between enantiomers, 14 or to entropic effects.…”