4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride as an enantioseparation enhancer for fluorescence chiral derivatization–liquid chromatographic analysis of dl-lactic acid

Todoroki, Kenichiro; Goto, Kanoko; Nakano, Tatsuki; Ishii, Yasuhiro; Min, Jun Zhe; Inoue, Kōichi; Toyo’oka, Toshimasa

doi:10.1016/j.chroma.2014.07.077

Cited by 13 publications

(8 citation statements)

References 26 publications

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“…Using the present 3D-HPLC system, the LA enantiomers Until now, several methods have been developed for the determination of the total LA in food/beverage products. Only a few methods, including an enzymatic method [25], capillary electrophoresis (CE) [26] and HPLC [24,28], have been developed for the determination of LA enantiomers, and were mainly applied to the yogurts. The enzymatic reactions of D-lactic dehydrogenase and L-lactic dehydrogenase were used to determine the LA enantiomers in the plain yogurts, and the concentrations of the D-and L-LA were 29.0 -122.2 and 75.1 -116.1 μmol/mL, respectively [25].…”

Section: Enantioselective Determination Of La In Various Food/beverage Samplesmentioning

confidence: 99%

“…The LA levels in the yogurts observed by the method were 67.8 μmol/g for D-LA and 43.3 μmol/g for L-LA, and the %D value was 61.0. A chiral derivatization method using (S)-(+)-4-(N,Ndimethylaminosulfonyl)-7-(3-aminopyrrolidin-1-yl)-2,1,3benzoxadiazole was also applied to various foodstuffs [28].…”

Section: Enantioselective Determination Of La In Various Food/beverage Samplesmentioning

confidence: 99%

“…For the determination of the LA enantiomers in foods, several methods have been reported [24][25][26][27][28]. Among them, the chromatographic methods are the most widely used techniques.…”

Section: Introductionmentioning

confidence: 99%

“…Among them, the chromatographic methods are the most widely used techniques. A method using the chiral derivatization reagent, (S)-(+)-4-(N,N-dimethylaminosulfonyl)-7-(3aminopyrrolidin-1-yl)-2,1,3-benzoxadiazole to form the diastereomers was published and applied to the analysis of DL-LA in foodstuffs [28]. A chiral mobile phase method applying N,N-dipropyl-L-alanine and copper (II) acetate as the chiral additive was also reported and used to determine the LA enantiomers in fermented dairy products [24].…”

Section: Introductionmentioning

confidence: 99%

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Chiral Analysis of Lactate in Various Food Samples Including Japanese Traditional Amber Rice Vinegar and the Developmental Changes During Fermentation Processes

et al. 2021

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Enantioselective analysis of lactate (LA) in various fermented food/beverage samples including the Japanese traditional amber rice vinegars was performed using a newly designed three-dimensional high-performance liquid chromatographic (3D-HPLC) system. The enantiomers of LA are reported to be possible biomarkers for some diseases such as diabetic mellitus. To evaluate the diagnostic value, the dietary intake should be taken into consideration. Therefore, clarifying the presence of LA enantiomers in our environment is a matter of interest. In the present study, LA enantiomers in a variety of fermented food/beverage samples were determined after the pre-column derivatization with 4-nitro-7-piperazino-2,1,3-benzoxadiazole. Among the fermented products tested, high concentrations of LA enantiomers were observed in a Japanese traditional amber rice vinegar (sample SK, 13.1 and 22.8 μmol/mL for D-LA and L-LA, respectively). The developmental changes of the LA enantiomers during the fermentation/aging processes of the Japanese traditional amber rice vinegar were also studied. The concentrations of D-and L-LA drastically increased in the early stage of the fermentation and attained to the highest concentrations after 1 month, then gradually decreased thereafter. The present results help to illuminate the benefits of Japanese traditional vinegars in the health and food sciences.

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Section: Enantioselective Determination Of La In Various Food/beverage Samplesmentioning

confidence: 99%

Section: Enantioselective Determination Of La In Various Food/beverage Samplesmentioning

confidence: 99%

“…For the determination of the LA enantiomers in foods, several methods have been reported [24][25][26][27][28]. Among them, the chromatographic methods are the most widely used techniques.…”

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Chiral Analysis of Lactate in Various Food Samples Including Japanese Traditional Amber Rice Vinegar and the Developmental Changes During Fermentation Processes

et al. 2021

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“…For instance, most existing chiral derivatization agents are ineffective when used for D-and L-lactic acids (LAs) analysis because diastereoisomeric DL-LA derivatives tend to have only small differences in their tertiary structures. We found that 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMT-MM) [17][18][19] functions not only as a condensing agent but also as an enantioseparation enhancer for fluorescence diastereoisomeric derivatization of D-and L-LAs [20]. In this derivatization, the triazine unit of DMT-MM etherified the hydroxyl group of the LA derivative via an α-rearrangement reaction to produce a sterically bulky derivative.…”

Section: Introductionmentioning

confidence: 99%

4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium Chloride as an Enantioseparation Enhancer for Chiral Derivatization-LC Analysis of D- and L-Amino acids

et al. 2016

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We have developed a high-resolution chiral derivatization-LC method for the determination of D-and L-amino acids using 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMT-MM) as an enantioseparation enhancer. In this method, D-and L-amino acids were derivatized with (S)-(-)-1-(naphthyl)ethylamine (NEA) in the presence of DMT-MM as a condensing agent. These conditions resulted in the amino group of the D-and L-amino acid-NEA derivative being introduced in the triazine unit of DMT-MM, producing sterically bulky diastereoisomers. The resulting derivatives of the D-and L-amino acids could be discriminated and successfully enantioseparated through reversed-phase LC. This enantioseparation enhancement effect was demonstrated when using six other commercially available chiral amines as derivatization reagents. Since triazine modification possesses high ESI-responsivity, they showed higher sensitivities than non-triazine derivatives. The developed derivatization method was successfully applied to highly sensitive quantification of D-and L-amino acids by combining LC-MS/MS analysis.

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A photonic crystal fiber–based fluorescence sensor for simultaneous and sensitive detection of lactic acid enantiomers

Chi

et al. 2022

Anal Bioanal Chem

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Graphical abstract A photonic crystal fiber (PCF)–based fluorescence sensor is developed for rapid and sensitive detection of lactic acid (LA) enantiomers in serum samples. The sensor is fabricated by chemical binding dual enzymes on the inner surface of the PCF with numerous pore structures and a large specific surface area, which is suitable to be utilized as an enzymatic reaction carrier. To achieve simultaneous detection of l -LA and d -LA, the PCF with an aldehyde-activated surface is cut into two separate pieces, one of which is coated with l -LDH/GPT enzymes and the other with d -LDH/GPT enzymes. By being connected and carefully aligned to each other by a suitable sleeve tube connector, the responses of both l -LA and d -LA sensors are determined by laser-induced flourescence (LIF) detection. With the aid of enzyme-linked catalytic reactions, the proposed PCF sensor can greatly improve the sensitivity and analysis speed for the detection of LA enantiomers. The PCF sensor exhibits a low limit of detection of 9.5 μM and 0.8 μM, and a wide linear range of 25–2000 μM and 2–400 μM for l -LA and d -LA, respectively. The sensor has been successfully applied to accurate determination of LA enantiomers in human serum with satisfactory reproducibility and stability. It is indicated that the present PCF sensors would be used as an attractive analytical platform for quantitative detection of trace-amount LA enantiomers in real biological samples, and thus would play a role in disease diagnosis and clinical monitoring in point-of-care testing. Supplementary Information The online version contains supplementary material available at 10.1007/s00216-021-03788-5.

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4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride as an enantioseparation enhancer for fluorescence chiral derivatization–liquid chromatographic analysis of dl-lactic acid

Cited by 13 publications

References 26 publications

Chiral Analysis of Lactate in Various Food Samples Including Japanese Traditional Amber Rice Vinegar and the Developmental Changes During Fermentation Processes

Chiral Analysis of Lactate in Various Food Samples Including Japanese Traditional Amber Rice Vinegar and the Developmental Changes During Fermentation Processes

4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium Chloride as an Enantioseparation Enhancer for Chiral Derivatization-LC Analysis of D- and L-Amino acids

A photonic crystal fiber–based fluorescence sensor for simultaneous and sensitive detection of lactic acid enantiomers

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