Formation and Verification of the Structure of the 1-Fluorenylmethyl Chloroformate Derivative of Sulfamethazine

Sulfamethazine (SMZ) is derivatized with 1-fluorenylmethyl chloroformate (FMOC) to form the fluorescent adduct SMZ−FMOC. Conditions for formation are optimized with respect to pH, reagent concentration, and reagent ratio. Reagent and product profiles (including the hydrolysis byproduct FMOC-OH) vers...

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Bibliographic Details
Published in:Analytical chemistry (Washington) 1996-01, Vol.68 (1), p.86-92
Main Authors: Liang, Gao Shan (Sam), Zhang, Zane (Zhi Yu), Baker, Warren L, Cross, Reginald F
Format: Article
Language:English
Subjects:
Chemistry
Drugs
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Summary:Sulfamethazine (SMZ) is derivatized with 1-fluorenylmethyl chloroformate (FMOC) to form the fluorescent adduct SMZ−FMOC. Conditions for formation are optimized with respect to pH, reagent concentration, and reagent ratio. Reagent and product profiles (including the hydrolysis byproduct FMOC-OH) versus time are followed by reversed phase HPLC with UV absorbance detection. FMOC−SMZ has been crystallized, its composition confirmed by microanalysis, and its structure corroborated by IR and NMR spectroscopy. From 10 down to 1 ppm, there is clear gentle curvature in the fluorescence intensity of SMZ−FMOC. The linear response range extends from above 100 ppb down to about 100 ppt, and an increase in sensitivity for the fluorescent detection of FMOC−SMZ (over the usual UV absorbance detection of SMZ) is calculated to be better than 3 orders of magnitude.
ISSN:0003-2700
1520-6882
DOI:10.1021/ac9505280