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

被引：39

作者：

Katritzky, Alan R. ^{[1
]}

Tala, Srinivasa R. ^{[1
]}

Abo-Dya, Nader E. ^{[1
,2
]}

Gyanda, Kapil ^{[1
]}

El-Gendy, Bahaa El-Dien M. ^{[1
,3
]}

Abdel-Samii, Zakaria K. ^{[2
]}

Steel, Peter J. ^{[4
]}

机构：

[1] Univ Florida, Dept Chem, Ctr Heterocycl Cpds, Gainesville, FL 32611 USA

[2] Zagazig Univ, Fac Pharm, Dept Organ Pharmaceut Chem, Zagazig, Egypt

[3] Benha Univ, Fac Sci, Dept Chem, Banha, Egypt

[4] Univ Canterbury, Dept Chem, Christchurch 1, New Zealand

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 18期

关键词：

NATIVE CHEMICAL LIGATION; CONTAINING PEPTIDE SEQUENCES; AMINO-ACIDS; ACYLATION; REAGENTS; CYSTEINE; ACYLBENZOTRIAZOLES; EFFICIENT; FMOC-ALPHA-AMINOACYL)BENZOTRIAZOLES; DERIVATIVES;

D O I：

10.1021/jo900853s

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：7165 / 7167

页数：3

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