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.
Graduate Institute of Pharmaceutical Sciences, Collage of Pharmacy, Kaohsiung Medical University, Kaohsiung, 807, Taiwan.
Tang-Chia
TC
Chung
Wung-Pung
WP
Su
Hwang-Shang
HS
Kou
Yu-Ting
YT
Lin
Min-Yuan
MY
Hung
Hsin-Lung
HL
Wu
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