1-Pyrenylboronic Acid as a Reactive Matrix for the Analysis of Polyfunctional Compounds by MALDI Mass Spectrometry: New Possibilities

Abstract 1-Pyrenylboronic acid (1-PBA) is a type of a reactive matrix useful for the analysis of polyfunctional compounds by MALDI mass spectrometry. It exhibits conventional matrix properties (absorption and transfer of laser radiation energy) and acts as a derivatizing reagent capable of interacting with vicinal functional groups under mild conditions and forming covalent adducts. Pyrenyl group in its structure, which has high ability to absorb UV laser quanta, ensures the detection of analyte derivatives containing a 1-PBA residue as radical cations, which is untypical for MALDI. The effectiveness of its use was earlier proved for compounds containing 1,2-diol fragments. This work presents additional cases of using this reactive matrix in the analysis of practically significant compounds of this type, demonstrating that 1-PBA can also react with distant OH groups. Many examples show its applicability to the study of various α-hydroxy acids and vicinal aminols and capability of forming cyclic covalent adducts with 1,2-diamines.