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

J Org Chem. 2009 Sep 18;74(18):7165-7. doi: 10.1021/jo900853s.

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-e 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 CIGAR-gHMBC experiments. The structure of compound 8d was also supported by single-crystal X-ray diffraction.

MeSH terms

  • Acetonitriles / chemistry
  • Acylation
  • Cysteine* / analogs & derivatives
  • Cysteine* / chemical synthesis
  • Cysteine* / chemistry
  • Ethylamines / chemistry
  • Magnetic Resonance Spectroscopy
  • Models, Chemical
  • Nitrogen / chemistry*
  • Sulfur / chemistry*
  • Triazoles / chemistry
  • Water / chemistry
  • X-Ray Diffraction

Substances

  • Acetonitriles
  • Ethylamines
  • Triazoles
  • Water
  • Sulfur
  • Cysteine
  • Nitrogen
  • triethylamine