Novel Insights into the Maillard Catalyzed Degradation of Maltose

Smuda, Mareen; Glomb, Marcus A.

doi:10.1021/jf203346b

Cited by 52 publications

(98 citation statements)

References 33 publications

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“…Consequently, there must be alternative precursors for oxalic acid-Q formation to oxalic acid itself. 3,4-DDP is a known intermediate of maltose degradation but was found in neither the glucose nor ASA reaction systems (38). Hence, the origin of the detected 3,4-DDP-Q remains unknown.…”

Section: Discussionmentioning

confidence: 99%

“…In Maillard chemistry, glyoxylic acid is assigned to disaccharide chemistry (38) but can also arise from oxidation of glyoxal (68) and degradation of DHA (65,69). However, this cannot account solely for the plasma levels, which were 2.5-fold higher than GO and in the same range as 2,3-DKG.…”

Section: Discussionmentioning

confidence: 99%

“…The quinoxaline derivatives of the ␣-DCs will be marked hereafter with the suffix "-Q". 1-DG-Q, 3-DG-Q, glucosone-Q, Lederer's glucosone-Q, 1-DP-Q, 3-DP-Q, 3,4-DDP-Q, pentosone-Q, 1-DT-Q, 3-DT-Q, threosone-Q, pyruvic acid-Q, glyoxylic acid-Q, oxalic acid-Q, and 3-DG were synthesized according to our previous work (37)(38)(39). The identities of target compounds were verified by nuclear magnetic resonance (NMR) experiments.…”

Section: Methodsmentioning

confidence: 99%

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Extending the Spectrum of α-Dicarbonyl Compounds in Vivo

Henning¹,

Liehr²,

Girndt

et al. 2014

Journal of Biological Chemistry

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114

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Background: ␣-Dicarbonyls are central intermediates in the formation of advanced glycation end products (AGEs). Results: A quantitation method for the complete spectrum relevant in vivo was established. Conclusion: Non-enzymatic chemistry of glucose and L-ascorbic acid as precursors and ␣-dicarbonyl intermediates play an important role in vivo. Significance: Knowledge of plasma levels of ␣-dicarbonyls is crucial to understand the complex pathways of AGE formation in vivo.

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Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

See 1 more Smart Citation

Extending the Spectrum of α-Dicarbonyl Compounds in Vivo

Henning¹,

Liehr²,

Girndt

et al. 2014

Journal of Biological Chemistry

Self Cite

114

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“…Thus, the level of DDMP may be substantially affected by the degree of beer ageing and redox status. Smuda and Glomb (2011) depicted the importance of the redox processes during Maillard degradation of maltose. They suggest 1-amino acid-1,4-dideoxyglucosulose as a highly potent player to undergo intermolecular redox reactions.…”

Section: Beersmentioning

confidence: 99%

Effect of Maillard reaction on reducing power of malts and beers

Čechovská¹,

Konečný²,

Velı́šek³

et al. 2012

Czech J. Food Sci.

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AbstractČechovská L., Konečný M., Velíšek J., Cejpek K. (2012): Effect of Maillard reaction on reducing power of malts and beers. Czech J. Food Sci., 30: 548-556.HPLC with amperometric detection was used to evaluate the reducing power of 23 beers and aqueous extracts of 17 barley malts. While brew pale malts were only slightly higher in electrochemical reducing capacity than natural barleys (about 1.3 g BHAE/kg), caramel malts with the colour of 60-450°EBC showed 7.5-17.2 g BHAE/kg. The superior reducing power of the darker caramel malts was partly due to the presence of a Maillard-derived 2,3-dihydro-3,5-dihydroxy-6-methyl-(4h)-pyran-4-one (DDMP), which was responsible for 21-55% of their electrochemical capacity. Among common brew malts, only the Munich type showed a significantly increased electrochemical capacity -6.8 ± 0.8 g BHAE/kg. In addition to the malts, the brewing can also affect the electrochemical capacity of beers, which ranged from 0.4 ± 0.1 to 1.9 ± 0.3 g BHAE/l. Simple indigenous malt-derived phenolics were responsible for 48-57% of capacity in pale lagers and for 33-45% of it in dark and other specialty lagers. DDMP was not detected in most pale lagers, while it was responsible for up to 11% of the electrochemical capacity in dark and special beers. Highmolecular-weight fraction (> 1kDa) of beers comprised 19-39% (pale lagers) and 14-21% (dark and special beers) of the capacity. The reducing power of malts and beers determined by the amperometric method was confirmed by a good correlation with the results of DPPH• scavenging assay.

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“…However, saccharides that contain α-1,6 bonds, such as isomaltose and panose, are not used up during E. coli fermentation because E. coli cannot assimilate isomaltose and panose as carbon sources. Furthermore, these sugars, which contain reducing sugar moieties, can react with free amino groups of amino acids during the purification step (Smuda and Glomb 2011;Ledl and Schleicher 1990); this so-called Maillard reaction decreases the yield of the final product and contaminates the reaction mixture with undesirable compounds. These problems must be overcome in order to increase the yield and productivity of fermentation when using glucose feedstock as a carbon source.…”

Section: Introductionmentioning

confidence: 99%

Engineering of Escherichia coli to facilitate efficient utilization of isomaltose and panose in industrial glucose feedstock

Abe¹

2017

J Adv Chem Eng

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Industrial glucose feedstock prepared by enzymatic digestion of starch typically contains significant amounts of disaccharides such as maltose and isomaltose and trisaccharides such as maltotriose and panose. Maltose and maltosaccharides can be utilized in Escherichia coli fermentation using industrial glucose feedstock because there is an intrinsic assimilation pathway for these sugars. However, saccharides that contain α-1,6 bonds, such as isomaltose and panose, are still present after fermentation because there is no metabolic pathway for these sugars. To facilitate more efficient utilization of glucose feedstock, we introduced glvA, which encodes phospho-α-glucosidase, and glvC, which encodes a subunit of the phosphoenolpyruvate-dependent maltose phosphotransferase system (PTS) of Bacillus subtilis, into E. coli. The heterologous expression of glvA and glvC conferred upon the recombinant the ability to assimilate isomaltose and panose. The recombinant E. coli assimilated not only other disaccharides but also trisaccharides, including alcohol forms of these saccharides, such as isomaltitol. To the best of our knowledge, this is the first report to show the involvement of the microbial PTS in the assimilation of trisaccharides. Furthermore, we demonstrated that an L-lysineproducing E. coli harboring glvA and glvC converted isomaltose and panose to L-lysine efficiently. These findings are expected to be beneficial for industrial fermentation.

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Novel Insights into the Maillard Catalyzed Degradation of Maltose

Cited by 52 publications

References 33 publications

Extending the Spectrum of α-Dicarbonyl Compounds in Vivo

Extending the Spectrum of α-Dicarbonyl Compounds in Vivo

Effect of Maillard reaction on reducing power of malts and beers

Engineering of Escherichia coli to facilitate efficient utilization of isomaltose and panose in industrial glucose feedstock

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