Simultaneous analysis of DL-Amino acids in foods and beverages using a highly sensitive chiral resolution labeling reagent

Ozaki, Makoto; Nakade, Tomomi; Shimotsuma, Motoshi; Ikeda, Akari; Kuranaga, Takefumi; Kakeya, Hideaki; Hirose, Tsunehisa

doi:10.1016/j.jchromb.2024.124239

Journal of Chromatography B

2024

DOI: 10.1016/j.jchromb.2024.124239

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Simultaneous analysis of DL-Amino acids in foods and beverages using a highly sensitive chiral resolution labeling reagent

Makoto Ozaki,

Tomomi Nakade,

Motoshi Shimotsuma

et al.

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Cited by 3 publications

References 38 publications

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Twisted Amide‐Mediated Peptide Synthesis

Koyama,

Kuranaga,

Suo

et al. 2024

Chemistry A European J

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A robust, practical, and sustainable isomerization‐suppressed peptide bond formation via acyl sulfonamide, a twisted amide, is disclosed. Tosyl isocyanate and pentafluorobenzyl bromide were applied in combination to activate the peptide C‐terminus, which then reacted with an amine to yield an elongated peptide with high stereochemical purity. Careful analysis of NMR spectra of the active intermediate revealed the presence of an intramolecular hydrogen bond, suggesting that the hydrogen bond suppressed Cα‐epimerization during amidation. The isomerization suppression by the intramolecular hydrogen bond is expected to be effective even under high dilution conditions, making the present method a powerful tool for the synthesis of complex macrocyclic peptides. In addition to peptide synthesis, the developed synthetic entry to twisted amides can be applied to the investigation of transition metal‐catalyzed N–C bond activation. Moreover, the application to the N–C bond activation returned insight into peptide synthesis, leading to the use of sulfonamide as a protecting group of carboxylic acid that can be orthogonally removed in the presence of other conventional protecting groups.

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Twisted Amide‐Mediated Peptide Synthesis

Koyama,

Kuranaga,

Suo

et al. 2024

Chemistry A European J

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Simultaneous Analysis of Imidazole Dipeptides, Constituent Amino Acids, and Taurine in Meats Using the Highly Sensitive Labeling Reagent l-FDVDA and PBr Column

Ozaki,

Nakade,

Sekiguchi

et al. 2024

J. Agric. Food Chem.

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Imidazole dipeptides (IDPs) are found in the skeletal muscles and brains of various animals, and they exhibit unique functions like antioxidant and antiaging properties. Despite their importance, the metabolic mechanisms and physiological roles of IDPs remain unclear. Herein, we propose a method for the simultaneous analysis of IDPs, their constituent amino acids, and taurine, which are difficult to separate using conventional labeling reagents or columns, using liquid chromatography−single quadrupole mass spectrometry with PBr column and our highly sensitive labeling reagent, 1-fluoro-2,4-dinitrophenyl-5-L-valine-N,Ndimethylethylenediamineamide (L-FDVDA). This method successfully separated histidine and carnosine enantiomers as well as L-2oxocarnosine with high antioxidant activity under the same conditions. Our labeling reagent was more stable than the other reagents and did not degrade and desorb from the analytes for at least 1 week at 4 °C. Furthermore, our method allows for the accurate analysis of IDPs, amino acids, and taurine in meats from various animal species, tissues, and breeds.

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Chiral resolution of dl-leucine via salifying tartaric acid derivatives

Shi,

Guo,

Luo

et al. 2025

CrystEngComm

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Simultaneous analysis of DL-Amino acids in foods and beverages using a highly sensitive chiral resolution labeling reagent

Cited by 3 publications

References 38 publications

Twisted Amide‐Mediated Peptide Synthesis

Twisted Amide‐Mediated Peptide Synthesis

Simultaneous Analysis of Imidazole Dipeptides, Constituent Amino Acids, and Taurine in Meats Using the Highly Sensitive Labeling Reagent l-FDVDA and PBr Column

Chiral resolution of dl-leucine via salifying tartaric acid derivatives

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