Isolation, identification, and proposed formation mechanism of a novel hydrophilic compound formed by Maillard reaction between pyridoxamine and pentose

Pyridoxamine (PM) could competitively protect amino groups in proteins from glycating agents. Although PM is expected to react with saccharides, available data therein are limited. In this study, a novel hydrophilic compound from a model reaction solution containing PM and xylose was isolated and id...

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Bibliographic Details
Published in:Scientific reports 2020-02, Vol.10 (1), p.1823-1823, Article 1823
Main Authors: Nomi, Yuri, Otsuka, Yuzuru
Format: Article
Language:English
Subjects:
140/131
631/1647/2230/1378
631/1647/2258/878/1263
Amino acids
Amino groups
Chromatography
Diabetes
Glucose
Humanities and Social Sciences
Investigations
Life sciences
Maillard reaction
multidisciplinary
Peptides
pH effects
Proteins
Saccharides
Science
Science (multidisciplinary)
Spectrum analysis
Xylose
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Summary:Pyridoxamine (PM) could competitively protect amino groups in proteins from glycating agents. Although PM is expected to react with saccharides, available data therein are limited. In this study, a novel hydrophilic compound from a model reaction solution containing PM and xylose was isolated and identified as (6a R ,9a R )-1,8,9-trihydroxy-2,6a-dimethyl-6a,9a-dihydrocyclopenta[5,6]pyrano[3,4- c ]pyridin-7(5 H )-one with a tricyclic structure. This compound appeared to be specifically formed from pentose via 1-deoxypentosone, and its formation was facilitated over a pH range of 7.0–8.0. After heating at 90 °C for 5 h in a reaction mixture containing 30 mM PM and pentose at pH 7.4, this compound was obtained at a yield of 6.95–8.53 mM.
ISSN:2045-2322
2045-2322
DOI:10.1038/s41598-020-58727-8