A non-fluorescent derivative from derivatizing trans, trans-muconic acid with 2-(2-naphthoxy)ethyl-2-(piperidino)ethanesulfonate.
trans, trans-Muconic acid (MA) is a polar metabolite of benzene and used as a biomarker for monitoring human exposure to benzene. Because MA is a trace metabolite, sensitive method is required for its detection. In addition, MA is a highly polar compound with dicarboxyl functions that could incur unfavorable adsorption on silica-based stationary phase usually used for separation. To address these problems, we planned to derivatize MA with a fluorescent reagent 2-(2-naphthoxy)ethyl-2-(piperidino)ethanesulfonate to give a naphthoxy derivative of MA for improving detection sensitivity and chromatographic properties. Surprisingly, the resulting derivative shows no fluorescent activity (lambda(ex): 226 nm; lambda(em): 350 nm). The negative results could be used as an instructive example for discussing on fluorescence quenching.
Chung
Tang-Chia
TC
Graduate Institute of Pharmaceutical Sciences, Collage of Pharmacy, Kaohsiung Medical University, Kaohsiung, 807, Taiwan.
Su
Wung-Pung
WP
Kou
Hwang-Shang
HS
Lin
Yu-Ting
YT
Hung
Min-Yuan
MY
Wu
Hsin-Lung
HL
D005470:Fluorometry; D006801:Humans; D057927:Hydrophobic and Hydrophilic Interactions; D013058:Mass Spectrometry; D010880:Piperidines / Q000737:chemistry*; D013011:Sorbic Acid / Q000031:analogs & derivatives* / Q000032:analysis / Q000737:chemistry; D013237:Stereoisomerism; D013438:Sulfhydryl Compounds / Q000737:chemistry*
C549154:2-(2-naphthoxy)ethyl-2-(piperidino)ethanesulfonate; D010880:Piperidines; D013438:Sulfhydryl Compounds; C005939:muconic acid; D013011:Sorbic Acid