Peptide and Amino Acid Glycation: New Insights into the Maillard Reaction

Abstract

For Abstract see ChemInform Abstract in Full Text.

Building blocks for the synthesis of post‐translationally modified glycated peptides and proteins

“…In contrast from what was previously reported for short postsynthetically glycated peptides, in which the incorporated sugar moiety presents several tautomeric forms in equilibrium [21,22], the sugar moiety of N ε -Amadori-containing N α -Fmoc-Lys-OH derivatives 1 and 1a displays a single β-pyranose tautomer (NMR data). The β-pyranose form, which is the predominant tautomer of glucose in solution, is also the only detectable tautomer in 1 and 1a.…”

Characterization of Site-Specific Glycation During Process Development of a Human Therapeutic Monoclonal Antibody

“…This reaction is also commonly referred to as a Maillard reaction after the name of the inventor. 21,22 As glucose is the major source of energy in the cell culture media, small amounts of glycation in mAbs during cell culture can be expected. [23][24][25] The majority of this glycation is distributed over greater than 30 lysine residues.…”

Direct glucosone-based synthesis and HILIC-ESI-MS/MS characterization of N-terminal fructosylated valine and valylhistidine for validation of enzymatic HbA1c assays in the diagnosis of diabetes mellitus

“…Although the synthesis and characterization of many fructosylated amino acids and peptides have been reported in literature, the majority study kinetics of their formation, specific analytical data, or the reported synthetic approaches lead to unsatisfying yields or purities [13][14][15][16][17]. Only few information about their isolation in good yields and purities has been reported, using either protected sugars as presented by the groups of Hoffmann and Horvat [18][19][20] or zinc halide catalysts as by the groups of Harohally and Norin [21][22][23]. The synthetic approach that mimics the natural reaction of free Glc with a primary amine of a protein occurring in the organism is currently still widely used by working groups studying Amadori compounds or developing HbA 1c assays [24][25][26][27][28].…”