Chromatographic profiles of tryptophan and kynurenine enantiomers derivatized with (S)‐4‐(3‐isothiocyanatopyrrolidin‐1‐yl)‐7‐(N, N‐dimethylaminosulfonyl)‐2, 1, 3‐benzoxadiazole using LC–MS/MS on a triazole‐bonded column. Issue 10 (21st July 2017)

• Record Type: Journal Article
• Authors: Iizuka, Hideaki; Harashima, Takahiro; Takahashi, Shuhei; Kuwabara, Ryosuke; Naito, Yoko; Sakamoto, Tatsuya; Onozato, Mayu; Ichiba, Hideaki; Fukushima, Takeshi
• Is Part Of: Chirality. Volume 29:Issue 10(2017)
• Page Start: 603
• Page End: 609
• Publication Date: 2017-07-21
• Subjects: chiral derivatization -- d, l‐kynurenine -- d, l‐tryptophan -- solid‐phase extraction -- tandem MS -- triazole‐bonded column; Chirality -- Periodicals; Pharmaceutical chemistry -- Periodicals; 541.22
• DOI: 10.1002/chir.22726
• Languages: English
• ISSNs: 0899-0042

Abstract

Abstract: d ‐ andl ‐Tryptophan (Trp) andd ‐ andl ‐kynurenine (KYN) were derivatized with a chiral reagent, ( S )‐4‐(3‐isothiocyanatopyrrolidin‐1‐yl)‐7‐(N, N‐dimethylaminosulfonyl)‐2, 1, 3‐benzoxadiazole (DBD‐PyNCS), and were separated enantiomerically by high‐performance liquid chromatography (HPLC) equipped with a triazole‐bonded column (Cosmosil HILIC) using tandem mass spectrometric (MS/MS) detection. Effects of column temperature, salt (HCO2 NH4 ) concentration, and pH of the mobile phase in the enantiomeric separation, followed by MS detection of ( S )‐DBD‐PyNCS‐d, l ‐Trp and ‐d, l ‐KYN, were investigated. The mobile phase consisting of CH3 CN/10 mM ammonium formate in H2 O (pH 5.0) (90/10) with a column temperature of 50–60 °C gave satisfactory resolution ( R s) and mass‐spectrometric detection. The enantiomeric separation ofd, l ‐Trp andd, l ‐KYN produced R s values of 2.22 and 2.13, and separation factors (α) of 1.08 and 1.08, for the Trp and KYN enantiomers, respectively. The proposed LC–MS/MS method provided excellent detection sensitivity of both enantiomers of Trp and KYN (5.1–19 nM). Abstract :