3-(D-Erythro-Trihydroxypropyl)-1-Neopentyl Pyrrole-2-Carboxaldehyde. A Novel Nonenzymatic Browning Product of Glucose

Abstract

The reaction of equimolar amounts of D-glucose and neopentyl-amine in phosphate buffer under physiological conditions of pH and temperature has been investigated. From the diethyl ether extract, we have identified a C-8 condensation product and have demonstrated that its formation does not proceed via a free-radical mechanism. Based on ¹H and ¹³C NMR and other spectroscopic techniques, including UV, IR, EI-MS, CI-MS of the TMS derivative, the structure 3-(D-erythro-trihydroxypropyl)-1-neopentyl pyrrole-2-carboxaldehyde, was assigned to this advanced Maillard reaction product.