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Investigation and kinetic evaluation of the reactions of hydroxymethylfurfural with amino and thiol groups of amino acids.
Food Chem. 2018 Feb 01; 240:354-360.FC

Abstract

In this study, reactions of hydroxymethylfurfural (HMF) with selected amino acids (arginine, cysteine and lysine) were investigated in HMF-amino acid (high moisture) and Coffee-amino acid (low moisture) model systems at 5, 25 and 50°C. The results revealed that HMF reacted efficiently and effectively with amino acids in both high and low moisture model systems. High-resolution mass spectrometry (HRMS) analyses of the reaction mixtures confirmed the formations of Michael adduct and Schiff base of HMF with amino acids. Calculated pseudo-first order reaction rate constants were in the following order; kCysteine>kArginine>kLysine for high moisture model systems. Comparing to these rate constants, the kCysteine decreased whereas, kArginine and kLysine increased under the low moisture conditions of Coffee-amino acid model systems. The temperature dependence of the rate constants was found to obey the Arrhenius law in a temperature range of 5-50°C under both low and high moisture conditions.

Authors+Show Affiliations

Food Quality and Safety (FoQuS) Research Group, Department of Food Engineering, Hacettepe University, 06800 Beytepe, Ankara, Turkey.Food Quality and Safety (FoQuS) Research Group, Department of Food Engineering, Hacettepe University, 06800 Beytepe, Ankara, Turkey. Electronic address: vgokmen@hacettepe.edu.tr.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

28946283

Citation

Hamzalıoğlu, Aytül, and Vural Gökmen. "Investigation and Kinetic Evaluation of the Reactions of Hydroxymethylfurfural With Amino and Thiol Groups of Amino Acids." Food Chemistry, vol. 240, 2018, pp. 354-360.
Hamzalıoğlu A, Gökmen V. Investigation and kinetic evaluation of the reactions of hydroxymethylfurfural with amino and thiol groups of amino acids. Food Chem. 2018;240:354-360.
Hamzalıoğlu, A., & Gökmen, V. (2018). Investigation and kinetic evaluation of the reactions of hydroxymethylfurfural with amino and thiol groups of amino acids. Food Chemistry, 240, 354-360. https://doi.org/10.1016/j.foodchem.2017.07.131
Hamzalıoğlu A, Gökmen V. Investigation and Kinetic Evaluation of the Reactions of Hydroxymethylfurfural With Amino and Thiol Groups of Amino Acids. Food Chem. 2018 Feb 1;240:354-360. PubMed PMID: 28946283.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Investigation and kinetic evaluation of the reactions of hydroxymethylfurfural with amino and thiol groups of amino acids. AU - Hamzalıoğlu,Aytül, AU - Gökmen,Vural, Y1 - 2017/07/26/ PY - 2017/05/29/received PY - 2017/07/13/revised PY - 2017/07/25/accepted PY - 2017/9/27/entrez PY - 2017/9/28/pubmed PY - 2017/11/29/medline KW - Amino acids KW - Hydroxymethylfurfural KW - Michael addition KW - Reaction kinetics KW - Schiff base formation SP - 354 EP - 360 JF - Food chemistry JO - Food Chem VL - 240 N2 - In this study, reactions of hydroxymethylfurfural (HMF) with selected amino acids (arginine, cysteine and lysine) were investigated in HMF-amino acid (high moisture) and Coffee-amino acid (low moisture) model systems at 5, 25 and 50°C. The results revealed that HMF reacted efficiently and effectively with amino acids in both high and low moisture model systems. High-resolution mass spectrometry (HRMS) analyses of the reaction mixtures confirmed the formations of Michael adduct and Schiff base of HMF with amino acids. Calculated pseudo-first order reaction rate constants were in the following order; kCysteine>kArginine>kLysine for high moisture model systems. Comparing to these rate constants, the kCysteine decreased whereas, kArginine and kLysine increased under the low moisture conditions of Coffee-amino acid model systems. The temperature dependence of the rate constants was found to obey the Arrhenius law in a temperature range of 5-50°C under both low and high moisture conditions. SN - 1873-7072 UR - https://www.unboundmedicine.com/medline/citation/28946283/Investigation_and_kinetic_evaluation_of_the_reactions_of_hydroxymethylfurfural_with_amino_and_thiol_groups_of_amino_acids_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0308-8146(17)31285-2 DB - PRIME DP - Unbound Medicine ER -
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