Enantioselective supramolecular devices in the gas phase. Resorcin[4]arene as a model system

Abstract

This review describes the state-of-art in the field of the gas-phase reactivity of diastereomeric complexes formed between a chiral artificial receptor and a biologically active molecule. The presented experimental approach is a ligand-displacement reaction carried out in a nano ESI-FT-ICR instrument, supported by a thermodynamic MS-study and molecular-mechanics and molecular-dynamics (MM/MD) computational techniques. The noncovalent ion-molecule complexes are ideal for the study of chiral recognition in the absence of complicating solvent and counterion effects.

Keywords: diastereomeric complexes; gas phase enantioselectivity; kinetics; mass spectrometry; resorcin[4]arene receptor.

Figure 1

Examples of monoexponential decay: The slope of the line directly provides the reaction pseudo-first-order rate constant.

Figure 2

Example of biexponential decay.

Figure 3

Amidoresorcin[4]arene Y_S.

Scheme 1

Studied (a) peptidoresorcin[4]arenes and (b) dipeptidic guests.

Figure 4

Catharanthine and vindoline, monomers constituting the anticancer vinblastine and the analogous vincristine.

Figure 5

Stable conformers of catharanthine.

Figure 6

Global minima of (a) [V_S∙H∙T]⁺ and (b) [V_R∙H∙T]⁺ complexes.

Figure 7

Guests studied in [47].

Figure 8

Selected nucleosides.

Figure 9

Example of molecular logic gate.

Figure 10

Cyclochiral resorcin[4]arenes.