Selective synthesis and structural elucidation of S-acyl- and N-acylcysteines

Alan R. Katritzky; Srinivasa R. Tala; Nader E. Abo-Dya; Kapil Gyanda; Bahaa El Dien M El-Gendy; Zakaria K. Abdel-Samii; Peter J. Steel

doi:10.1021/jo900853s

Selective synthesis and structural elucidation of S-acyl- and N-acylcysteines

Alan R. Katritzky, Srinivasa R. Tala, Nader E. Abo-Dya, Kapil Gyanda, Bahaa El Dien M El-Gendy, Zakaria K. Abdel-Samii, Peter J. Steel

Medicinal Chemistry

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Abstract

(Chemical Equation Presented) N-(Acyl)-1H-benzotriazoles 6a-f react with L-cysteine 5 at 20°C to give exclusively (i) N-acyl-L-cysteines 8a-e in the presence of triethylamine in CH₃CN-H₂O (3:1), but (ii) S-acyl-L-cysteines 7a-e in CH₃CN-H₂O (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 ¹H-¹⁵N CIGAR-gHMBC experiments. The structure of compound 8d was also supported by single-crystal X-ray diffraction.

Original language	English (US)
Pages (from-to)	7165-7167
Number of pages	3
Journal	Journal of Organic Chemistry
Volume	74
Issue number	18
DOIs	https://doi.org/10.1021/jo900853s
State	Published - Sep 18 2009

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title = "Selective synthesis and structural elucidation of S-acyl- and N-acylcysteines",

abstract = "(Chemical Equation Presented) N-(Acyl)-1H-benzotriazoles 6a-f react with L-cysteine 5 at 20°C to give exclusively (i) N-acyl-L-cysteines 8a-e in the presence of triethylamine in CH3CN-H2O (3:1), but (ii) S-acyl-L-cysteines 7a-e in CH3CN-H2O (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 1H-15N CIGAR-gHMBC experiments. The structure of compound 8d was also supported by single-crystal X-ray diffraction.",

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AU - Katritzky, Alan R.

AU - Tala, Srinivasa R.

AU - Abo-Dya, Nader E.

AU - Gyanda, Kapil

AU - El-Gendy, Bahaa El Dien M

AU - Abdel-Samii, Zakaria K.

AU - Steel, Peter J.

PY - 2009/9/18

Y1 - 2009/9/18

N2 - (Chemical Equation Presented) N-(Acyl)-1H-benzotriazoles 6a-f react with L-cysteine 5 at 20°C to give exclusively (i) N-acyl-L-cysteines 8a-e in the presence of triethylamine in CH3CN-H2O (3:1), but (ii) S-acyl-L-cysteines 7a-e in CH3CN-H2O (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 1H-15N CIGAR-gHMBC experiments. The structure of compound 8d was also supported by single-crystal X-ray diffraction.

AB - (Chemical Equation Presented) N-(Acyl)-1H-benzotriazoles 6a-f react with L-cysteine 5 at 20°C to give exclusively (i) N-acyl-L-cysteines 8a-e in the presence of triethylamine in CH3CN-H2O (3:1), but (ii) S-acyl-L-cysteines 7a-e in CH3CN-H2O (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 1H-15N CIGAR-gHMBC experiments. The structure of compound 8d was also supported by single-crystal X-ray diffraction.

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Selective synthesis and structural elucidation of S-acyl- and N-acylcysteines

Abstract

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