Reaction of 2-amino-2-deoxy-D-glucose and lysine: isolation and characterization of 2,5-bis(tetrahydroxybutyl)pyrazine

Carbohydr Res. 1988 Dec 31:184:67-75. doi: 10.1016/0008-6215(88)80006-5.

Abstract

The reaction of 2-amino-2-deoxy-D-glucose with lysine in water under simulated physiological conditions gave several browning products, with characteristic optical (lambda max 340 nm) and fluorescent properties (emission at 430 nm for excitation at 362 nm). The major product was isolated and characterized by mass spectrometry and n.m.r. spectroscopy as 2,5-bis(tetrahydroxybutyl)pyrazine derived by the condensation of two molecules of 2-amino-2-deoxy-D-glucose.

MeSH terms

  • Chemical Phenomena
  • Chemistry
  • Gas Chromatography-Mass Spectrometry / methods
  • Glucosamine*
  • Indicators and Reagents
  • Lysine*
  • Magnetic Resonance Spectroscopy / methods
  • Mass Spectrometry / methods
  • Pyrazines*
  • Spectrophotometry / methods

Substances

  • Indicators and Reagents
  • Pyrazines
  • tagatosazine
  • Lysine
  • Glucosamine