Saccharide induced racemization of amino acids in the course of the Maillard reaction

Brückner, Hans; Justus, Josena; Kirschbaum, Jochen

doi:10.1007/s007260170007

Cited by 35 publications

(31 citation statements)

References 6 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…heated aqueous solutions of l-AAs with/without excess saccharides for 96 h at pH 7.0 and 100℃, and showed that saccharides induced racemization of some l-AAs (Brückner et al, 2001). They acids were selected due to their reported high concentrations (d+l) in non-ripened mirin (Morita and Tanabe, 1970).…”

Section: Introductionmentioning

confidence: 99%

“…The racemization during thermal processing was attributed to the Maillard reaction. Brückner et alheated aqueous solutions of l-AAs with/without excess saccharides for 96 h at pH 7.0 and 100℃, and showed that saccharides induced racemization of some l-AAs (Brückner et al, 2001). They Y. Inoue et al 680 proposed that d-AAs were generated from Amadori rearrangement products (ARPs), which are stable intermediates formed in the course of the Maillard reaction.…”

mentioning

confidence: 99%

See 1 more Smart Citation

Mechanisms of d-Amino Acid Formation During Maturation of Sweet Rice Wine <i>(mirin)</i>

Inoue

Katsumata

Watanabe

et al. 2016

FSTR

View full text Add to dashboard Cite

(Gogami et al., 2006; Palla et al., 1989). Fermented foods were reported to have higher levels of d-AAs than perishable foods. In soy sauces, d-Ala, d-Asp, and d-Glu were detected at concentrations of 1.6, 0.9, and 1.0 mM, respectively, with corresponding levels in cheese of 5.8, 4.4, and 4.8 mM, respectively (all numbers are average values for eight products, Inoue et al., 2014). Balsamic vinegar matured for twenty-five years contained a high amount of d-Pro (1.7 mM, Erbe et al., 1998). Other fermented foods, including soybean paste (Inoue et al., 2014), black vinegar (Okada et al., 2011, and sake (Japanese alcoholic beverage, Gogami et al., 2011), were reported to contain several d-AAs. d-AAs are thought to be produced by lactic acid bacteria in fermented foods (Gogami et al., 2012), with their racemase enzymes being responsible for the conversion of l-amino acids (l-AAs) into d-AAs during the fermentation process.In addition to perishable and fermented foods, processed plant syrup, roasted cocoa beans, and thermally-treated bee honey were reported to have high relative amounts of d-AAs compared to the total d+l amino acid content (Pätzold and Brückner, 2005; Pätzold and Brückner, 2006a, 2006b). The racemization during thermal processing was attributed to the Maillard reaction. Brückner et al.heated aqueous solutions of l-AAs with/without excess saccharides for 96 h at pH 7.0 and 100℃, and showed that saccharides induced racemization of some l-AAs (Brückner et al., 2001). They Y. Inoue et al. 680 proposed that d-AAs were generated from Amadori rearrangement products (ARPs), which are stable intermediates formed in the course of the Maillard reaction.Sweet rice wines (mirins) are alcoholic condiments high in glucose that are used as a seasoning in Japanese cuisine, and those matured for longer periods are considered to be key ingredients for top-level cuisine. Mirin is produced from glutinous rice, koji malt (non-glutinous rice malted using Aspergillus oryzae), and distilled spirit, and is saccharified at room temperature for around two months (conversion of starch into glucose). After filtration, some mirins are immediately made into seasoning products (usually by adding liquid sugar), whereas others are stored at room temperature for long periods to ripen in the presence of high concentrations of alcohol and glucose, thereby developing a well-balanced sweet flavor (Kawabe and Morita, 1998). Several reactions occur between the components during maturation, including the Maillard reaction.In fact, the amounts of 3-deoxyglucosone, which is one of the sugar degradation products, and browning compounds, which absorb light at 430 nm indicating the progress of the Maillard reaction were reported to be high in ripened mirins (Takahashi and Takemura, 2011). In addition, some ARPs (fructosyl histidine and fructosyl methionine) were identified as the compounds exhibiting antioxidative activities in mirins (Ishizaki et al., 2006). Few studies, however, were concerned with the chirality of amino acids in non-ripene...

show abstract

Section: Introductionmentioning

confidence: 99%

mentioning

confidence: 99%

Mechanisms of d-Amino Acid Formation During Maturation of Sweet Rice Wine <i>(mirin)</i>

Inoue

Katsumata

Watanabe

et al. 2016

FSTR

View full text Add to dashboard Cite

show abstract

“…Recently, heating experiments of synthetic Amadori compounds proved that they are sources of amino acid-enantiomers (8). Furthermore, convincing evidence has been recently established that D-amino acids are formed in the course of the Maillard reaction (6,8).…”

Section: Introductionmentioning

confidence: 99%

“…Brückner et al (6) have recently pointed out that D-amino acids are formed on heating aqueous solutions of L-amino acids (2.5 mM) together with an excess (278 mM) of saccharides (glucose, fructose, and saccharose) at 100 o C for 24～96 h in aqueous solutions of pH 2.5 (AcOH) or pH 7.0 (NaOAc). Thus, the formation of D-amino acids in many foods of plant and animal origin are the results of non-enzymic browning since the presence of amino acids together with saccharides is common.…”

Section: Introductionmentioning

confidence: 99%

“…The degree of racemization depends in particular on steric and electronic properties of the amino acid side chains. It should be noted that the early stages of the Maillard reaction proceeds already under mild conditions (6) and do not reThe Effect of pH on the Antioxidative Activity of Melanoidins 183 quire alkaline or acidic condition. This new racemization mechanism based on the releatively stable Amadori compounds has been used to explain the generation of free D-amino acid in foods such as dried fruits, concentrated plant juices and fortified wines (7).…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

The Effect of pH on the Antioxidative Activity of Melanoidins Formed from Glucose and Fructose with L and D-Asparagine in the Maillard Reaction

Kim¹,

Lee²

2008

JFN

View full text Add to dashboard Cite

In this study, the effect of pH on the antioxidative activities of melanoidins formed as a result of the reaction between sugars, glucose (Glc) or fructose (Fru), and amino acids, L-asparagine (L-Asn) and D-asparagine (D-Asn) are examined. For this purpose, antioxidative activities were evaluated on the basis of reducing power, including ferric reducing/antioxidant power (FRAP) and free radical scavenging activity includes 1,1-diphenyl-2-picryl-hydrazil (DPPH) and 2,2'-azinobis(3-ethylbenothiazoline-6-sulfonic acid) diammonium salt (ABTS) and ferrous ion chelating activity. Ethylene diamine tetraacetate (EDTA) and trolox, a water-soluble analog of tocopherol, were used as reference antioxidant compounds. The antioxidative activities of the melanoidins at a pH of 7.0 were greater than those with a pHs of 4.0 and pH 10.0. Especially, it was found that the melanoidins formed from D-isomers are more effective antioxidants in different in vitro assays. The reducing power and chelating activity of the melanoidins formed from the Fru systems were higher than those of the melanoidins formed from the Glc systems. However, the ABTS radical scavenging activity of the melanoidins formed from the Glc systems were higher than those of the melanoidins formed from the Fru systems. In particular, the DPPH radical scavenging activity and the FRAP of the melanoidins showed different antioxidative activities according to pH level.

show abstract

Marfey's reagent: Past, present, and future uses of 1‐fluoro‐2,4‐dinitrophenyl‐5‐L‐alanine amide

B’Hymer¹,

Montes-Bayón²,

Caruso³

2003

J of Separation Science

View full text Add to dashboard Cite

This article describes some of the uses of Marfey's reagent, 1-fluoro-2,4-dinitrophenyl-5-L-alanine amide (FDAA), a pre-column derivatizing reagent for the separation of enantiomeric isomers of amino acids and amine compounds. An introduction to the basic implementation of this reagent and its historical development are presented. Actual uses in amino acid, short peptide, and pharmaceutical compounds are included, as well as the advantages and disadvantages over other pre-column derivatization techniques and direct chromatographic separations. Applications of current interest, including its use as an orthogonal analysis and in enantiomeric purity analysis of selenoamino acids using element specific detection, are also discussed.

show abstract

Saccharide induced racemization of amino acids in the course of the Maillard reaction

Cited by 35 publications

References 6 publications

Mechanisms of d-Amino Acid Formation During Maturation of Sweet Rice Wine <i>(mirin)</i>

Mechanisms of d-Amino Acid Formation During Maturation of Sweet Rice Wine <i>(mirin)</i>

The Effect of pH on the Antioxidative Activity of Melanoidins Formed from Glucose and Fructose with L and D-Asparagine in the Maillard Reaction

Marfey's reagent: Past, present, and future uses of 1‐fluoro‐2,4‐dinitrophenyl‐5‐L‐alanine amide

Contact Info

Product

Resources

About