Structure–reactivity relationship of Amadori rearrangement products compared to related ketoses

Kaufmann, Martín; Meissner, Philipp M.; Pelke, Daniel; Mügge, Clemens; Kroh, Lothar W.

doi:10.1016/j.carres.2016.04.016

Cited by 30 publications

(28 citation statements)

References 71 publications

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“…In chained keto molecule of N-(1-deoxy-D-xylulos-1-yl)-phenylalanine, intra molecular hydrogen bonds between 2-OH, 3-OH, and oxygen of carbonyl group of MRI keto-form, were possibly formed in aqueous solution. Similar results were previously reported based on 13 C NMR spectroscopic investigations, 28,30 revealing that the Amadori ketoses exists in aqueous solution as an equilibrium of different conformers including a-furanose and b-furanose, ring and open ring. 9,30 A tautomeric equilibrium involving ring 3.4.…”

Section: Analysis Of Prepared Mri By Nmrsupporting

confidence: 89%

Controlled formation of flavor compounds by preparation and application of Maillard reaction intermediate (MRI) derived from xylose and phenylalanine

et al. 2017

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Section: Analysis Of Prepared Mri By Nmrsupporting

confidence: 89%

Controlled formation of flavor compounds by preparation and application of Maillard reaction intermediate (MRI) derived from xylose and phenylalanine

et al. 2017

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“…The chemical shift (δ) of 206.00 in 13 C NMR shows the presence of the chained keto form ( N ‐(1‐deoxy‐D‐xylulos‐1‐yl)‐glutamic acid). Kaufmann, Meissner, Pelke, Mügge, and Kroh () studied several different conformations of Amadori ketose in aqueous medium by NMR and stated that intra molecular hydrogen bonds and cyclic keto‐forms could be formed between 2‐OH and 3‐OH in chained Amadori ketoses. Furthermore, there are several conformations, such as α‐furanose, β‐uranose ring formation, and ring opening.…”

Section: Resultsmentioning

confidence: 99%

Preparation of N‐(1‐Deoxy‐Α‐D‐Xylulos‐1‐Yl)‐Glutamic Acid via Aqueous Maillard Reaction Coupled with Vacuum Dehydration and Its Flavor Formation Through Thermal Treatment of Baking Process

Cui

Sun

et al. 2019

Journal of Food Science

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Amadori rearrangement product (ARP) derived from glutamic acid (Glu) and xylose (Xyl) was prepared by aqueous Maillard reaction. Subsequently, ion exchange chromatography, MS, and NMR were used for purification and identification, confirming that the molecular formula of ARP was C10H17NO8, namely N‐(1‐deoxy‐α‐D‐xylulos‐1‐yl)‐glutamic acid, with a molecular mass of 279 Da. To improve the aqueous yield of ARP, a thermal reaction coupled with vacuum dehydration was used and the yield of ARP was increased from 2.07% to 75.11%. Furthermore, flavor formation capacity of ARP by a thermal treatment simulated to a baking process was compared with Maillard reaction products, Maillard‐dehydration reaction products, and Glu‐Xyl mixture. The results indicated that a larger amount of volatile flavor compounds and a biscuit‐like, burnt aroma was generated rapidly from the mixture of ARP and unreacted Glu‐Xyl, which could be a potential flavor enhancer for baked foods. Practical Application Maillard reaction performed in aqueous medium through thermal reaction combined with vacuum dehydration is a novel and practical technology that could be widely used to produce Maillard reaction intermediates (MRIs), such as Amadori or Heyns rearrangement products, which are regarded as significant nonvolatile aroma precursors and have stable physical and chemical properties compared with Maillard reaction products (MRPs). MRI derived from glutamic acid and xylose is a potential substitute of MRPs for flavorings preparation and shows a great capacity to generate fresh flavors in a short time at high temperature, which meets the requirements of baking foods. Therefore, the new developed method could be a promising tool for MRI preparation and application in food and flavoring industries.

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“…The chemical shift δ of 206.05 ppm in 13 C NMR indicated that the chain ( N ‐(1‐deoxy‐ d ‐xylulos‐1‐yl)‐glutathione, 1 keto‐form) occurred in aqueous medium. It has been reported that intramolecular hydrogen bonds and cyclic ketones in the chain ARP might be derived from 2‐OH and 3‐OH, and the tautomerization provided a dynamic equilibrium between the different conformations of chain and ring, α‐furanose and β‐furanose (Kaufmann, Meissner, Pelke, Mugge, & Kroh, ). Because MGX contains a xylulose section, a tautomeric equilibrium including chain, ring, and keto‐enol tautomerization was proposed (Figure ).…”

Section: Resultsmentioning

confidence: 99%

Aqueous Preparation of Maillard Reaction Intermediate from Glutathione and Xylose and its Volatile Formation During Thermal Treatment

Sun

Cui

Zhan

et al. 2019

Journal of Food Science

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Maillard reaction intermediate (MGX) generated from glutathione and xylose in aqueous medium was prepared via the Maillard reaction performed under a two-stage temperature increase process. The purified MGX was identified by Fourier-transform infrared spectroscopy, mass spectrometry, and nuclear magnetic resonance as N-(1-deoxyd-xylulos-1-yl)-glutathione (Amadori compound, C 15 H 25 O 10 N 3 S) with five main isomers. The method of Maillard reaction performed under a two-stage temperature increase process was further verified by high-performance liquid chromatography. The optimal reaction time and temperature for the preparation of MGX was determined as 60 min at 90°C. The yield of MGX was increased from 8.60% to 55.52% through thermal reaction coupled with vacuum dehydration. In addition, rapid and more Maillard-type volatile compounds were formed in MGX during thermal treatment than that in Maillard reaction products or glutathione-xylose mixture. Beside, MGX possessed more pleasing meat-like volatile profile compared with the Amadori compound of glutamic acid-xylose (AAX), cysteine-xylose (ACX), and glycinexylose (AGX). Therefore, it suggested that the MGX had the potential to achieve a better flavor formation during thermal treatment.Keywords: a 2-stage temperature increase process, Maillard reaction intermediate, Maillard-type volatile formation, N-(1-deoxy-d-xylulos-1-yl)-glutathione, thermal treatmentPractical Application: Maillard reaction intermediates, such as Amadori or Heyns rearrangement products (ARP or HRP), are important flavor precursors, which possess stable physicochemical properties, but tend to degrade into flavor compounds at high temperatures. Maillard reaction intermediate from glutathione and xylose acts as primary flavor enhancers to complete Maillard reaction to produce flavors in the subsequent thermal processing, which can significantly improve and stabilize the flavor quality of the meaty food, and deserves a very broad application prospects. The new developed method will be a significant theoretical basis on research preparation and properties of Maillard reaction intermediates in complex food systems.

show abstract

Structure–reactivity relationship of Amadori rearrangement products compared to related ketoses

Cited by 30 publications

References 71 publications

Controlled formation of flavor compounds by preparation and application of Maillard reaction intermediate (MRI) derived from xylose and phenylalanine

Controlled formation of flavor compounds by preparation and application of Maillard reaction intermediate (MRI) derived from xylose and phenylalanine

Preparation of N‐(1‐Deoxy‐Α‐D‐Xylulos‐1‐Yl)‐Glutamic Acid via Aqueous Maillard Reaction Coupled with Vacuum Dehydration and Its Flavor Formation Through Thermal Treatment of Baking Process

Aqueous Preparation of Maillard Reaction Intermediate from Glutathione and Xylose and its Volatile Formation During Thermal Treatment

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