Synthesis of pyrraline reference material

Abstract

A simplified and improved method is described for the preparation of pyrraline, a lysine derivative from the advanced Maillard reaction and potential indicator for heat treatment of foods. The compound was obtained in a high degree of purity and with a yield of 31% from N alpha-t-butyloxycarbonyl-L-lysine after heating with 3-deoxy-D-erythro-hexos-2-ulose for 2 h at 70 degrees C in the dry state, preparative fractionation of the resulting N alpha-t-butyloxycarbonyl pyrraline with reverse-phase liquid chromatography and final deprotection of the intermediate compound with acetic acid.

Maillard Reaction of d-Glucose: Identification of a Colored Product with Conjugated Pyrrole and Furanone Rings

“…NMR spectroscopic data of both compounds agree in several relevant details, if the influence of substituents on the chemical shifts is taken into account.The furanone 3 is the predominant Maillard product of pentoses (1), whereas pyrrole aldehydes of type 2 are formed by reaction of D-glucose with primary amines (3,4).…”

Ovalbumin Modified with Pyrraline, a Maillard Reaction Product, shows Enhanced T-cell Immunogenicity

“…Modification of OVA with pyrraline (Pyr-OVA) was performed as described by Henle and Bachmann (22). Briefly, 3-deoxyglucosone (3-DG) and OVA were dissolved in 0.1 N sodium acetate buffer at a 4:1 ratio to lysine residues.…”

Comparative LC–MS/MS profiling of free and protein-bound early and advanced glycation-induced lysine modifications in dairy products

“…The chemical syntheses of ( 13 C 2 )-CML, ( 13 C 6 , 15 N 2 )-FL and ( 13 C 6 , 15 N 2 )-Pyr were developed by Delatour and Henle, and have already been reported elsewhere in sufficient detail [30][31][32].Therefore, the conditions are only briefly described hereafter.…”