Enantioselective photolysis and quantitative chiral analysis of tryptophan complexed with alkali-metalized L-serine in the gas phase.

Abstract

The enantioselective photolysis of a cold gas-phase noncovalent complex of tryptophan with alkali-metalized L-serine, M(+) (L-Ser)(Trp) (M = Na and Li), was examined using a tandem mass spectrometer containing a variable-temperature ion trap. CO2 loss from Trp in the clusters was enantiomerically selective in ultraviolet excitation with linearly polarized light. M(+) (L-Ser) promoted the enantioselective photolysis of Trp as a chiral auxiliary. The enantioselective photolysis of the D-enantiomer was applied to a quantitative chiral analysis, in which the optical purity of tryptophan could be determined by measuring the relative abundance ratio R of the enantioselective CO2 loss to the chiral-independent evaporation of L-Ser in a single photodissociation mass spectrum of M(+) (L-Ser)(Trp).