Synthesis of novel fluorogenic Edman reagents, 7-N,N-dimethylaminosulphonyl- 4-(2,1,3-benzoxadiazolyl)isothiocyanate (DBD-NCS) and 7-aminosulphonyl-4-(2,1,3-benzoxadiazolyl)isothiocyanate (ABD-NCS)

Biomed Chromatogr. 1993 Jan-Feb;7(1):56-7. doi: 10.1002/bmc.1130070114.

Abstract

Novel fluorogenic Edman reagents, 7-N,N-dimethylaminosulphonyl-4- (2,1,3-benzoxadiazolyl)isothiocyanate (DBD-NCS) and 7-aminosulphonyl-4-(2,1,3-benzoxadiazolyl)isothiocyanate (ABD-NCS) having no fluorescence themselves were synthesized. The derivatives of amino acids with DBD-NCS fluorescence at 505 nm with excitation at 385 nm. They were separated on a reversed-phase HPLC column and detected at the sub-picomol level. Ala-Phe derivatized with DBD-NCS was cleaved by acid to generate DBD-thiocarbamyl-Ala.

MeSH terms

  • Amino Acid Sequence
  • Amino Acids / analysis
  • Chromatography, High Pressure Liquid
  • Dipeptides / analysis
  • Fluorescent Dyes / chemical synthesis*
  • Indicators and Reagents
  • Isothiocyanates*
  • Molecular Sequence Data
  • Oxadiazoles / chemical synthesis*
  • Spectrophotometry, Ultraviolet
  • Thiocyanates / chemical synthesis*

Substances

  • Amino Acids
  • Dipeptides
  • Fluorescent Dyes
  • Indicators and Reagents
  • Isothiocyanates
  • Oxadiazoles
  • Thiocyanates
  • 7-N,N-dimethylaminosulfonyl-4-(2,1,3-benzoxadiazolyl)isothiocyanate
  • 7-aminosulfonyl-4-(2,1,3-benzoxadiazolyl)isothiocyanate