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

Research output: Contribution to journal › Article › peer-review

41 Scopus citations

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
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.",

author = "Katritzky, \{Alan R.\} and Tala, \{Srinivasa R.\} and Abo-Dya, \{Nader E.\} and Kapil Gyanda and El-Gendy, \{Bahaa El Dien M.\} and Abdel-Samii, \{Zakaria K.\} and Steel, \{Peter J.\}",

year = "2009",

month = sep,

day = "18",

doi = "10.1021/jo900853s",

language = "English",

volume = "74",

pages = "7165--7167",

journal = "Journal of Organic Chemistry",

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TY - JOUR

T1 - Selective synthesis and structural elucidation of S-acyl- and N-acylcysteines

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.

UR - https://www.scopus.com/pages/publications/70249129814

U2 - 10.1021/jo900853s

DO - 10.1021/jo900853s

M3 - Article

C2 - 19697896

AN - SCOPUS:70249129814

SN - 0022-3263

VL - 74

SP - 7165

EP - 7167

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 18

ER -

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

Abstract

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