Development of a Derivatization Reagent with a 2-Nitrophenylsulfonyl Moiety for UHPLC-HRMS/MS and Its Application to Detect Amino Acids Including Taurine

Abstract

Taurine (Tau) has some important ameliorating effects on human health and is present in bivalve. For the selective analysis of Tau with other amino acids, we designed a derivatization reagent, 2,5-dioxopyrrolidin-1-yl(4-(((2-nitrophenyl)sulfonyl)oxy)-6-(3-oxomorpholino)quinoline-2-carbonyl)pyrrolidine-3-carboxylate (Ns-MOK-β-Pro-OSu). After derivatization with Ns-MOK-β-Pro-OSu, amino acids with Tau in Japanese littleneck clams were determined through ultra-high-performance-liquid chromatography with high-resolution tandem mass spectrometry (UHPLC-HRMS/MS) using an octadecyl silica column. We could detect 18 amino acids within 10 min. Tau, valine, glutamine, glutamic acid, and arginine in the clams were determined in the negative ion mode using the characteristic fragment ion, C6H4N1O5S, which corresponded to the 2-nitrobenzenesulfonylate moiety. The fragment ion, C6H4N1O5S, was recognized as a common feature regardless of the amino acid to be derivatized, and it was convenient for detecting amino acid derivatives with high selectivity and sensitivity. Therefore, highly selective quantification using UHPLC-HRMS/MS was possible using Ns-MOK-β-Pro-OSu.

Change in Metabolomic Profile Associated with an Average Increase in Plain Water Intake of >+1 L/Day, Sustained Over 4 Weeks, in Healthy Young Men with Initial Total Water Intake Below 2 L/Day

“…Features observed in other Adapt Study analyses of serum and urine, including sodium, potassium, vitamin D, and taurine, were not detected by the WCMC and not available in the metabolomic analysis dataset. Absence of their mention in the present analysis may reflect WCMC methods, which are tailored to describe primary metabolism, such as protocol that removes features considered to contribute noise, like sodium, or limitations related to ionization voltage so high that molecules like taurine fragment into multiple products [168,169].…”

Development of a Simple, Underivatized Method for Rapid Determination of Free Amino Acids in Honey Using Dilute-and-Shoot Strategy and Liquid Chromatography-Tandem Mass Spectrometry

“…Several studies have reported FAAs analysis using ion-exchange chromatography [ 9 ], capillary electrophoresis [ 10 ], gas chromatography [ 11 ] and high-performance liquid chromatography [ 12 ]. Owing to their high polarity and absence of specific chromophores, a derivatization step is usually required for FAAs before these analysis methods to improve detection sensitivity [ 13 , 14 ]. For example, a fully automated FAAs analyzer, which is frequently applied today, contains ion-exchange chromatography separation, post-column derivatization using ninhydrin reagent and ultraviolet detection under 570 nm or 440 nm.…”