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Preparation of 1-Amino-1-deoxyfructose Derivatives by Stepwise Increase of Temperature in Aqueous Medium and Their Flavor Formation Compared with Maillard Reaction Products

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Abstract

A novel method of Maillard reaction performed under stepwise increase of temperature was proposed for the preparation of Maillard reaction intermediate (MRI) derived from fructose (Fru) and phenylalanine (Phe). The optimal formation conditions of MRI in aqueous medium were determined as follows: pH 7.4 and heating for 100 min at 100 °C. The purified MRI was characterized to be 1-amino-1-deoxyfructose derivative (C15H21NO7, 327 Da) by mass spectrometry and NMR. The methodological effectiveness of this new developed method was further verified. Although almost similar types of volatile compounds were identified in the three heated solutions of Fru-Phe mixture, Maillard reaction products (MRPs) and 1-amino-1-deoxyfructose derivatives, the concentration of total volatile compounds was 118.30 μg/L relative to the internal standard for Fru-Phe mixture and increased by 64.49 and 1024.64 μg/L for MRPs and 1-amino-1-deoxyfructose derivative, respectively. The results showed that more fresh flavors were controlled formed from 1-amino-1-deoxyfructose derivative compared with those from MRPs or Fru-Phe mixture during the subsequent heating treatment; thus, the 1-amino-1-deoxyfructose derivatives could be a great potential substitute of unstable MRPs or Fru-Phe mixture in preparation of flavoring.

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Abbreviations

MRPs :

Maillard reaction products

Fru :

fructose

Phe :

phenylalanine

Cys :

cysteine

RP-HPLC :

reversed phase high performance liquid chromatography

UPLC :

ultra performance liquid chromatography

MS :

mass spectrometry

HS-SPME :

headspace solid phase microextraction

GC :

gas chromatography

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Funding

The research was supported by the Science and Technology Key Project of State Tobacco Monopoly Administration 110201402039, the National Natural Science Foundation of China 31671826, and the National Key Research and Development Program of China 2017YFD0400105.

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Correspondence to Jun Yang.

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The authors declare no competing financial interest.

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Yang, J., Deng, S., Yin, J. et al. Preparation of 1-Amino-1-deoxyfructose Derivatives by Stepwise Increase of Temperature in Aqueous Medium and Their Flavor Formation Compared with Maillard Reaction Products. Food Bioprocess Technol 11, 694–704 (2018). https://doi.org/10.1007/s11947-017-2039-4

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  • DOI: https://doi.org/10.1007/s11947-017-2039-4

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