Selective Synthesis and Structural Elucidation of S-Acyl- and N-Acylcysteines

Faculty Pharmacy Year: 2009
Type of Publication: Article Pages: 7165-7167
Authors:
Abo-Dya, Nader E, Katritzky, Alan R, Abdel-Samii, Zakaria K, Tala, Srinivasa R, Gyanda, Kapil, El-Gendy, Bahaa El-Dien M, Steel, Peter J
DOI: 10.1021/jo900853s
Journal: JOURNAL OF ORGANIC CHEMISTRY AMER CHEMICAL SOC Volume: 74
Research Area: Chemistry ISSN ISI:000269656400033
Keywords : Selective Synthesis , Structural Elucidation , S-Acyl- , N-Acylcysteines    
Abstract:
N-(Acyl)-1H-benzotriazoles 6a-f react with L-cysteine 5 at 20 degrees C to give exclusively (i) N-acyl-L-cysteines 8a-e in the presence of triethylamine in CH(3)CN-H(2)O (3: 1), but (ii) S-acyl-L-cysteines 7a-c in CH(3)CN-H(2)O (5:1) in the absence of base. Structures 7b, 7d and 8b, 8d are supported by 2D NMR spectroscopic methods including gDQCOSY, gHMQC, gHMBC, and (1)H-(15)N CIGA-RgH M BC experiments. The structure of compound 8d was also supported by single-crystal X-ray diffraction.
    
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