The synthesis of pure Amadori rearrangement products

Abstract

Recueil des Traoaux Chimiques desThe term "Maillard reaction" is used to describe a complex set of reactions in foods leading to flavour generation and non-enzymatic browning. The first step in this process is the so-called Amadori rearrangement: a reducing saccharide and a peptide fragment react to form an Amadori Rearrangement Product (ARP). To be able to do model studies on flavour generation, gram amounts of pure ARP are required. In the present study, glucose-derived ARPs were synthesised from specifically protected and activated starting compounds. After deprotection and purification, pure ARPs were obtained. This is the first time that ARPs of dipeptides have been isolated.

Lewis‐Acid‐Catalyzed Synthesis of Amadori and Heyns Dipeptides

“…One of the curios and important challenge was the application of Lewis acid‐catalyzed Amadori and Heyns reactions for the synthesis of glycopeptides. Significant efforts have been made for the application of Amadori and Heyns rearrangement reactions for the synthesis of glycopeptides [5–7] . One of the prominent approaches of achieving glycopeptides via Amadori and Heyns reactions involved the reaction of aldose/ketose with peptide in methanol/DMSO/pyridine solvent or phosphate buffer followed by the employment of suitable separation techniques for purification [5] .…”

“…Significant efforts have been made for the application of Amadori and Heyns rearrangement reactions for the synthesis of glycopeptides [5–7] . One of the prominent approaches of achieving glycopeptides via Amadori and Heyns reactions involved the reaction of aldose/ketose with peptide in methanol/DMSO/pyridine solvent or phosphate buffer followed by the employment of suitable separation techniques for purification [5] . The pure glycopeptides via Amadori/Heyns reaction were achieved only by the employment of column chromatography or ion chromatography techniques rendering the procedure not practical and economical [5–9] .…”

“…[5][6][7] One of the prominent approaches of achieving glycopeptides via Amadori and Heyns reactions involved the reaction of aldose/ketose with peptide in methanol/DMSO/pyridine solvent or phosphate buffer followed by the employment of suitable separation techniques for purification. [5] The pure glycopeptides via Amadori/Heyns reaction were achieved only by the employment of column chromatography or ion chromatography techniques rendering the procedure not practical and economical. [5][6][7][8][9] The glycopeptides incorporating carnosine/glutamyl proline have been recently accomplished in water, however, purity was achieved via preparative HPLC.…”

“…[5] The pure glycopeptides via Amadori/Heyns reaction were achieved only by the employment of column chromatography or ion chromatography techniques rendering the procedure not practical and economical. [5][6][7][8][9] The glycopeptides incorporating carnosine/glutamyl proline have been recently accomplished in water, however, purity was achieved via preparative HPLC. [10] In addition, one extreme case of purification has also been reported, wherein, after Heyns reaction of N-hippurly lysine with fructose, carboxypeptidase B was utilized to cleave hippuryl lysine and subsequent usage of preparative HPLC to accomplish pure Heyns peptide.…”