A three-step scheme to synthesize the 4-hydroxybutanoic acid (GHB) analog, 3-thio-4-hydroxybutanoic acid, was performed using 2(5H)-furanone as the starting material. In the presence of triethylamine, 2(5H)-furanone reacted with thioacetic acid at room temperature, producing 3-thioacetyl-4,5-dihyo-2(5H)-furanone. Under reflux, this intermediate product was treated with p-toluidine to make 3-thio-4,5-dihydro-2(5H)-furanone. Finally, in pH 12 solution, the majority of 3-thio-4,5-dihydro-2(5H)-furanone was hydrolyzed to 3-thio-4-hydroxybutanoic acid. TLC and 1H NMR was used to determine purity of products. Thio-derivative of GHB was cross-linked to different proteins for the development of anti-GHB ELISA, which was confirmed using MALDI mass spectrometry.

Synthesis and cross-linking of 3-thio-4-hydroxybutanoic acid to develop anti-GHB ELISA

240th National Meeting (2010)

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