Influence of 3-DG as a Key Precursor Compound on Aging of Lager Beers

Nobis, Arndt; Kunz, Oliver; Gastl, Martina; Hellwig, Michael; Henle, Thomas; Becker, Thomas

doi:10.1021/acs.jafc.0c08003

Cited by 13 publications

(14 citation statements)

References 32 publications

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“…14 It was found recently that the concentration of 3-DG in fresh beer correlates positively with the formation of these aldehydes during storage. 15 In higher animals, dietary 3-DG can be metabolized mainly by reduction to 3-deoxyfructose. 16−18 A minor pathway is the oxidation of 3-DG to 2-keto-3-deoxygluconic acid, which was found in erythrocytes.…”

Section: ■ Introductionmentioning

confidence: 99%

Reduction of 5-Hydroxymethylfurfural and 1,2-Dicarbonyl Compounds by Saccharomyces cerevisiae in Model Systems and Beer

Hellwig

Börner

Henle

2021

J. Agric. Food Chem.

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Glycation and caramelization reactions in malt lead to the formation of 1,2-dicarbonyl compounds, which come in contact with yeast during fermentation. In the present study, the metabolic fate of 5-hydroxymethylfurfural (HMF) and 1,2-dicarbonyl compounds (3-deoxyglucosone, 3-deoxygalactosone, 3-deoxypentosone, 3,4-dideoxyglucosone-3-ene) was assessed in the presence of Saccharomyces cerevisiae. HMF is degraded very fast by yeast with the formation of 2,5-bis(hydroxymethyl)furan (BHMF). By contrast, only 7–30% of 250 μM dicarbonyl compounds is degraded within 48 h. The respective deoxyketoses, 3-deoxyfructose (3-DF), 3-deoxytagatose, 3-deoxypentulose, and 3,4-dideoxyfructose, were identified as metabolites. While 17.8% of 3-deoxyglucosone was converted to 3-deoxyfructose, only about 0.1% of 3-deoxypentosone was converted to 3-deoxypentulose during 48 h. Starting with the parent dicarbonyl compounds, the synthesis of all deoxyketose metabolites was achieved by applying a metal-catalyzed reduction in the presence of molecular hydrogen. In a small set of commercial beer samples, BHMF and all deoxyketoses were qualitatively detected. 3-DF was quantitated in the four commercial beer samples at concentrations between 0.4 and 10.1 mg/L.

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Section: ■ Introductionmentioning

confidence: 99%

Reduction of 5-Hydroxymethylfurfural and 1,2-Dicarbonyl Compounds by Saccharomyces cerevisiae in Model Systems and Beer

Hellwig

Börner

Henle

2021

J. Agric. Food Chem.

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“…Ten kilograms of produced malts were milled using a type 16/16 two-roller mill from Künzel (Kulmbach, Bayern). The pilot brewhouse (80 L) was used as previously described in [13]. The grist was mashed in with 40 L standardized brewing liquor at 60 • C, and the temperature was raised to 62 • C. Two rests of 30 min each were held at 62 • C and 72 • C, after which the mash was raised to 78 • C and held for 10 min.…”

Section: Wort Production and Samplingmentioning

confidence: 99%

“…High-performance liquid chromatography, with ultraviolet detection (HPLC-UV) analytics and sample preparation, were applied as previously performed by Degen, Hellwig, and Henle [11] and modified as published by Nobis et al [13]. Wort samples were measured directly after derivatization and filtration (0.45 µm).…”

Section: Quantitation Of 3-dg and 3-dgalmentioning

confidence: 99%

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The Influence of Proteolytic Malt Modification on the Aging Potential of Final Wort

Nobis¹,

Lehnhardt²,

Gebauer³

et al. 2021

Foods

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The dynamic changes in beer flavor are determined by its aging potential, which comprises of present free and bound-state aldehydes and their precursors. Rising flavor-active aging compounds cause sensory deterioration (flavor instability). These compounds are mainly formed upstream in the brewing process through the Maillard reaction, the Strecker degradation, or lipid oxidation. Wort boiling is an especially critical production step for important reactions due to its high temperature and favorable pH value. Amino acid concentration, as an important aging-relevant precursor, is variable at the beginning of wort boiling, mainly caused by the malt modification level, and can further influence the aging potential aging formation during wort boiling. This study investigated the effect of the proteolytic malt modification level on the formation of precursors (amino acids and dicarbonyls) and free and bound-state aldehydes during wort boiling. Six worts (malt of two malting barley varieties at three proteolytic malt modification levels) were produced. Regarding precursors, especially Strecker, relevant amino acids and dicarbonyls increased significantly with an enhanced malt modification level. Concentrations of free and bound aldehydes were highest at the beginning of boiling and decreased toward the end. A dependency of malt modification level and the degree of free and bound aldehydes was observed for 2-methylpropanal, 2-methylbutanal, and 3-methylbutanal. Generally, a higher proteolytic malt modification level tended to increase free and bound aldehyde content at the end of wort boiling. Conclusively, the aging potential formation during boiling was increased by an intensified malt modification level.

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“…As a “protected glyoxal”, α-ketoacetals strategically direct nucleophiles to the less reactive carbonyl while protecting the more reactive aldehyde as an acetal; ,, furthermore, the acetal-protecting group, at the α-position, has even been reported to increase the reactivity of the adjacent carbonyl . This moiety is far more stable in ambient conditions than its deprotected counterpart, which makes α-ketoacetal compounds a satisfactory, practical, and advantageous substitute for the highly important dicarbonyl structural motif. ,,− Unfortunately, despite the auspicious potential of this functional group, to our knowledge, a programmable, yet inexpensive, method of α-ketoacetal synthesis has not been widely adopted in the literature. , Traditionally, α-ketoacetals are produced via diverse variations of selenium-catalyzed oxidations (Scheme a) − , or reactions of Grignard reagents and functionalized carbonyl compounds (Scheme b). , However, both of the foregoing reactions are limited by the necessity of harsh conditions, ,, extended reaction times, or sensitive synthetic setups and reagents. , …”

Section: Introductionmentioning

confidence: 99%

Rapid, One-Step Synthesis of α-Ketoacetals via Electrophilic Etherification

et al. 2021

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Herein, we report a rapid, one-step synthesis of α-ketoacetals via electrophilic etherification of α-alkoxy enolates and monoperoxyacetals. Methyl, primary, and secondary α-ketoacetals were obtained in 44–63% yields from tetrahydropyranyl substrates; using methyl tetrahydropyranyl, alkyl tetrahydropyranyl, or methyl tetrahydrofuranyl peroxyacetals, however, methyl and primary products were isolated in 66–90% yields. The present method is applied to C–O bond formation at tertiary carbons, via alkyl and methyl peroxyacetals, with yields of 25–65%. Intermolecular “alkoxyl” transfer, from peroxyacetal to α-alkoxy enolate, relies heavily on decreased steric bulk surrounding the peroxide bond and site of etherification; additionally, we found the α-OCH3 group to be critical in ensuring product formation. α-Ketoacetals demonstrated excellent reactivity, as selective, nucleophilic attack at the unprotected carbonyl furnished α-hydroxy acetals in 80–100% yields; subsequent hydrolysis of the foregoing compounds provided α-hydroxy aldehydes in yields of 58–90%.

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Influence of 3-DG as a Key Precursor Compound on Aging of Lager Beers

Cited by 13 publications

References 32 publications

Reduction of 5-Hydroxymethylfurfural and 1,2-Dicarbonyl Compounds by Saccharomyces cerevisiae in Model Systems and Beer

Reduction of 5-Hydroxymethylfurfural and 1,2-Dicarbonyl Compounds by Saccharomyces cerevisiae in Model Systems and Beer

The Influence of Proteolytic Malt Modification on the Aging Potential of Final Wort

Rapid, One-Step Synthesis of α-Ketoacetals via Electrophilic Etherification

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