Chiral Metabolomics Using Triazine-Based Chiral Labeling Reagents by UPLC-ESI-MS/MS.

The determination of enantiomers of biological molecules is an important issue because a significant difference in the activity of the enantiomers is generally observed in biological systems. Chiral separations can be carried out by direct resolution using a chiral stationary column or by indirect resolution based on the derivatization with a chiral reagent. Many chiral-labeling reagents for ultraviolet-visible and fluorescence detections have been developed for various functional groups, such as amine and carboxylic acid. However, there are hardly any labeling reagents for LC-MS-specific detection. Based on this observation, we have developed several chiral-labeling reagents for LC-MS/MS analysis.This chapter describes methodologies and applications for the indirect LC-MS/MS determination of biological chiral molecules using triazine-based chiral-labeling reagents, i.e., (S and R)-1-(4,6-dimethoxy-1,3,5-triazin-2-yl)pyrrolidin-3-amine (DMT-3(S and R)-Apy) for carboxylic acids and (S and R)-2,5-dioxopyrrolidin-1-yl-1-(4,6-dimethoxy-1,3,5-triazin-2-yl)pyrrolidine-2-carboxylate (DMT-(S and R)-Pro-OSu) for amines and amino acids. A reliable method for the non-targeted chiral metabolomics is also described in this chapter.