Formation of Deoxy-fructosazine and Its 6-Isomer on the Browning Reaction between Glucose and Ammonia in Weak Acidic Medium

Tsuchida, Hironobu; Kômoto, Masahiko; KATO, Hiromichi; Fujimaki, Masao

doi:10.1271/bbb1961.37.2571

Cited by 30 publications

(31 citation statements)

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“…2,6‐Deoxyfructosazine (2,6‐DOF) and 2,5‐deoxyfructosazine (2,5‐DOF) are very useful chemicals and have different applications, such as flavors in tobacco industry 22–24, treatment and prevention of diabetes (type II) 25, resistance of cancers 26, treatment of immunological and inflammatory disease 27, reagents for DNA strand cleavage 28. 2,6‐DOF and 2,5‐DOF have been prepared by reactions of glucose and fructose with ammonium salts 29, 30. The 2,5‐DOF and 2,6‐DOF were obtained in approximately equal ratio from the reaction of glucose with ammonium in weak acidic medium (pH 5.3∼6.0) 29, while the yield of 2,5‐DOF was much higher than that 2,6‐DOF in the reaction of fructose with ammonium formate 30.…”

Section: Introductionmentioning

confidence: 99%

Conversions of Cellobiose and Inulin to Deoxyfructosazine in Aqueous Solutions

Fan

Zhang

et al. 2011

CLEAN Soil Air Water

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The conversion of the biomass into high value-added chemicals is an attractive topic in green chemistry. In this work, we studied the synthesis of 2,6-deoxyfructosazine (2,6-DOF) and 2,5-deoxyfructosazine (2,5-DOF) from cellobiose and inulin, respectively, in aqueous solution by an one-pot two-step route. In this method, cellobiose or inulin was first hydrolyzed into glucose or fructose and then reacted directly with ammonium formate to form 2,6-DOF or 2,5-DOF. The effects of reaction temperature, reaction time, pH value on the yields of the products were studied. It was demonstrated that the cellobiose and inulin could be converted to 2,6-DOF and 2,5-DOF effectively at optimized condition.

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Section: Introductionmentioning

confidence: 99%

Conversions of Cellobiose and Inulin to Deoxyfructosazine in Aqueous Solutions

Fan

Zhang

et al. 2011

CLEAN Soil Air Water

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“…Kreatinin an der Bildung von m u t a g e n e n u n d k a n z e r o g e n e n Verbindun- (37,40,88,89). Kreatinin an der Bildung von m u t a g e n e n u n d k a n z e r o g e n e n Verbindun- (37,40,88,89).…”

Section: Abbau Der 3-desoxyosoneunclassified

Der Abbau von reduzierenden Zuckern und Aminen bei der Maillard-Reaktion

Ledl

1991

Z Ernährungswiss

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Through the Maillard reaction, occurring in food and in the human body, reducing sugars, amino acids and proteins are transformed. Some general and also specific degradation pathways for pentoses, mono- and disaccharides can be defined. The structures of the products are influenced by the type of amine (primary or secondary). During the degradation reactions C-C fissions of the sugars and amino acids (Strecker degradation) can be observed. Some Maillard products are suited as indicator substances to determine the extent of the Maillard reaction.

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“…Adenosine, for example, was analyzed using high-performance liquid chromatography HPLC (9) or capillary electrophoresis (10). Analysis of deoxyfructosazines (DFs) was less frequently reported in the peer reviewed literature (11,12). Descriptions of analytical procedures for glucosamine are more common because of the health-related implications of this compound.…”

Section: Introductionmentioning

confidence: 99%

Analysis of Certain Nitrogenous Compounds in Tobacco. Part 1: Adenosine, 2,5- and 2,6-Deoxyfructosazines, Mannosamine and Glucosamine

Moldoveanu

Byrd

Gerardi

2011

Beiträge Zur Tabakforschung International/Contributions to Tobacco Research

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Nitrogenous compounds such as amino acids and proteins are frequently analyzed in tobacco since they are considered precursors of toxicants in cigarette smoke. However, much less attention is given to other nitrogenous compounds such as amino sugars and deoxyfructosazines, although their concentration in tobacco can be equal to or even higher than that of most free amino acids. These nitrogenous compounds may contribute to the formation of toxicants in smoke, or may contribute to the sensory properties of cigarette smoke, reasons for which their analysis is important. This study describes a procedure for the analysis of adenosine, 2,5-and 2,6-deoxyfructosazines (DFs), mannosamine and glucosamine in tobacco. The analysis uses a liquid chromatography-tandem mass spectrometry (LC/MS/MS) technique. Sample preparation for analysis consists of the extraction of the tobacco with a solution of 90% water and 10% methanol, followed by filtration. The separation of the analytes was done on a hydrophilic interaction liquid chromatography HILIC column using an isocratic procedure with a solvent consisting of 78% CH 3 CN, 22% H 2 O, that also contained 0.1 % HCOOH and 0.143 g/L CH 3 COONH 4 . The measurements were done using electrospray positive ionization mass spectrometric detection. The analytical procedure was validated and was proven very reliable. A number of tobaccos were analyzed, including several fluecured and Burley USA tobaccos, off-shore tobaccos, two Oriental tobaccos, two green tobaccos, as well as tobaccos from commercial and Kentucky reference cigarettes. The ranges for the analytes per g tobacco were found between 0.4 and 20.3 µg/g for adenosine, between 0.0 and 608.5 µg/g for 2,5-DF, between 0.0 and 424.5 µg/g for 2,6-DF, between 12.5 and 415.5 µg/g for mannosamine and between 25.9 and 1885.7 µg/g for glucosamine.The study also indicated that the levels of DFs and that of the amino sugars in tobacco show a very good correlation. This correlation can be explained by the same source of the two classes of compounds, namely the reaction of (reducing) sugars and ammonia. [Beitr. Tabakforsch. Int. 24 (2011) 233-242] ZUSAMMENFASSUNG Stickstoffhaltige Verbindungen im Tabak, wie Aminosäuren und Proteine, werden häufig untersucht, da sie als Vorläufer für toxische Substanzen im Zigarettenrauch betrachtet werden. Dagegen wird anderen stickstoffhaltigen Verbindungen wie Aminozuckern und Deoxyfructosazinen weniger Aufmerksamkeit gewidmet, obwohl deren Konzentration im Tabak genauso groß oder sogar größer ist, als die von freien Aminosäuren. Dass diese stickstoffhaltigen Verbindungen zu der Bildung von toxischen Substanzen im Tabakrauch oder zu den sensorischen Eigenschaften von Zigarettenrauch beitragen können, sind wichtige Gründe für die Untersuchung. Diese Arbeit beschreibt ein Verfahren zur Analyse von Adenosin, 2,5-und 2,6-Deoxyfructosazinen (DFs), Mannosamin und Glucosamin im Tabak. Zur Analyse wurde eine liquid chromatography-tandem mass spectrometry (LC/MS/MS)-Technik verwendet. Die Probenvorbereitung für die ...

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Formation of Deoxy-fructosazine and Its 6-Isomer on the Browning Reaction between Glucose and Ammonia in Weak Acidic Medium

Cited by 30 publications

References 0 publications

Conversions of Cellobiose and Inulin to Deoxyfructosazine in Aqueous Solutions

Conversions of Cellobiose and Inulin to Deoxyfructosazine in Aqueous Solutions

Der Abbau von reduzierenden Zuckern und Aminen bei der Maillard-Reaktion

Analysis of Certain Nitrogenous Compounds in Tobacco. Part 1: Adenosine, 2,5- and 2,6-Deoxyfructosazines, Mannosamine and Glucosamine

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