HPLC–free method of synthesis of isotopically labeled deoxyfructosylated peptides

Kijewska, Monika; Zawadzka, Michalina; Włodarczyk, Karolina; Stefanowicz, Piotr

doi:10.1007/s00216-022-04022-6

Cited by 2 publications

(2 citation statements)

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“…Recently, Kijewska and co-workers have developed a functionalized resin�PhB-Lys(PhB)-Chem-Matrix Rink resin�that selectively and efficiently captures glycated peptides. 8,9 Furthermore, tags containing quaternary ammonium salt and phenylboronic acid derivatives, appropriately designed and synthesized, were used to increase the ionization efficiency of glycoconjugates in mass spectrometry analysis. 10,11 Furosine, formed by the hydrolysis of Amadori compounds, is usually detected by high-pressure liquid chromatography (HPLC), 12 ultra-pressure liquid chromatography (UPLC), or gas chromatography (GC) combined with fluorescence detection or mass spectrometry (MS).…”

Section: Introductionmentioning

confidence: 99%

“…Commercially available boronate-affinity materials (BAMs) are used to enrich samples in lactosylated peptides, , which allows the detection of low-concentration components of samples containing sugar moieties. Recently, Kijewska and co-workers have developed a functionalized resinPhB-Lys(PhB)-ChemMatrix Rink resinthat selectively and efficiently captures glycated peptides. , Furthermore, tags containing quaternary ammonium salt and phenylboronic acid derivatives, appropriately designed and synthesized, were used to increase the ionization efficiency of glycoconjugates in mass spectrometry analysis. , Furosine, formed by the hydrolysis of Amadori compounds, is usually detected by high-pressure liquid chromatography (HPLC), ultra-pressure liquid chromatography (UPLC), or gas chromatography (GC) combined with fluorescence detection or mass spectrometry (MS). , Lactosylation sites can be analyzed directly by MS or MS coupled with separation techniques, such as liquid chromatography (LC), ,,,, two-dimensional (2D) gel electrophoresis, , or capillary electrophoresis (CE). , The immunoassay techniques , are also applied. The advantage of mass spectrometry is its high sensitivity and specificity, which allows the identification and quantification of protein modification products.…”

Section: Introductionmentioning

confidence: 99%

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High-Temperature, Solid-Phase Reaction of α-Amino Groups in Peptides with Lactose and Glucose: An Alternative Mechanism Leading to an α-Ketoacyl Derivative

Kijewska

Zawadzka

Stefanowicz

2023

J. Agric. Food Chem.

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The reaction of proteins with reducing sugars results in the formation of Amadori products, which involves the Nterminal group and/or ε-amino group of the lysine side chain. However, less attention has been given to the reactivity of the Nterminus of a peptide chain under similar conditions. In our work, we focused on the reaction of the α-amino group of peptides in the presence of a reducing sugar, specifically lactose. We optimized the reaction conditions of model peptides with lactose in the solid phase and showed that temperatures above 120 °C lead to the deamination of the N-terminal amino acid moiety, ultimately resulting in α-ketoacids. We carried out detailed studies to confirm the structure of the deaminated product using analytical methods such as ESI-MS and LC−MS/MS, as well as chemical methods that involved the reduction of the carbonyl group combined with isotopic exchange and the reactivity of the carbonyl group with the hydroxylamine derivative. The structure of the reaction product was also confirmed by chemical synthesis. We suggested plausible mechanisms for the formation of the deaminated product and considered the probable path of its formation. Our aim was to determine whether the reaction proceeds according to the Streckerbased mechanism and direct imine isomerization by carrying out reactions of model peptides in the presence of lactose under aerobic and anaerobic conditions and comparing the results obtained. KEYWORDS: LC−MS/MS analysis, lactosylated peptides, α-ketoacid derivatives, deamination catalyzed by a reducing sugar ■ HIGHLIGHTS• LC−MS/MS analysis of lactosylated peptides.• Deamination of the N-terminal amino acid by a reducing sugar. • Chemoselective reaction of the hydroxylamine derivative with the deamination product.

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