Several 4-Substituted Glutamic Acid Derivatives and Small Peptides in Some Liliaceae Plants

Kasai, Takanori; Nishitoba, Tsuyoshi; Shiroshita, Yoshinari; Sakamura, Sadao

doi:10.1080/00021369.1984.10866487

Cited by 3 publications

(2 citation statements)

References 25 publications

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“…Homologs of monatin (γ-hydroxy-glutamic acid) in which the 3-indolylmethyl at C4 (γ-position) is replaced by various substituents, including methyl, ethyl, isobutyl, carboxymethyl, or carboxyethyl, are known as natural products. [15][16][17][18][19] These compounds, including monatin, must be produced via a com-mon biosynthetic pathway; i.e., a cross-aldol reaction and subsequent transamination. The basic structure of monatin is a substituted ketoglutaric acid, which must be constructed by a regiospecific cross-aldol reaction between pyruvic acid and indole-3-pyruvic acid.…”

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confidence: 99%

Preparation and Characterization of Four Stereoisomers of Monatin

et al. 2016

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Monatin is a naturally occurring, sweet amino acid comprising four stereoisomers due to its two asymmetric centers at C2 and C4. However, the characteristics of each stereoisomer have not yet been fully investigated. To obtain a sufficient amount of racemic monatin for optical resolution, a synthetic method was developed by modifying a possible biosynthetic pathway, i.e., a cross-aldol reaction and subsequent transamination. The key intermediate, 4-hydroxy-4-(3-indolylmethyl)-2-ketoglutaric acid, was obtained via the crossaldol reaction of pyruvic acid and indole-3-pyruvic acid. Subsequently, the carbonyl group was converted to a hydroxyimino group through reaction with hydroxylamine and then to an amino group via hydrogenation to produce monatin. Next, the racemic monatin was divided into mixtures of two pairs of enantiomers through recrystallization. Finally, both enantiomers of the N-carbobenzoxy-γ-lactone derivatives of monatin were separated by preparative HPLC and deprotected. It was found that all optically pure stereoisomers exhibited a sweet taste. The isomer that displayed the most intense sweetness was the (2R,4R)-isomer, as determined by single crystal X-ray structure analysis of the monatin potassium salt, whereas the least sweet isomer was the (2S,4S)-isomer, which demonstrated a far lower sweetness than was previously reported.

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Preparation and Characterization of Four Stereoisomers of Monatin

et al. 2016

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“…Based on the information about plant-derived substances with proven anti-cancer effect, we have structurally created compounds of group 5A-E: colchicine derivatives, neferine derivatives, 7-hydroxynuciferine derivatives, lycorine derivatives, 5,6-dehydroglycorine derivatives, and natural compounds conjugated with glutamic acid residues [ 28 , 72 , 73 , 74 , 75 , 76 , 77 , 78 , 79 , 80 , 81 , 82 , 83 , 84 , 85 , 86 , 87 , 88 , 89 ]. In addition, the hypothesis that conjugation with a single molecule of glutamic acid could bring benefits compared with the basic compounds of natural origin is being tested through computational studies.…”

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Identification of Some Glutamic Acid Derivatives with Biological Potential by Computational Methods

Moldovan,

Sandulea,

Lungu

et al. 2023

Molecules

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Glutamic acid is a non-essential amino acid involved in multiple metabolic pathways. Of high importance is its relationship with glutamine, an essential fuel for cancer cell development. Compounds that can modify glutamine or glutamic acid behaviour in cancer cells have resulted in attractive anticancer therapeutic alternatives. Based on this idea, we theoretically formulated 123 glutamic acid derivatives using Biovia Draw. Suitable candidates for our research were selected among them. For this, online platforms and programs were used to describe specific properties and their behaviour in the human organism. Nine compounds proved to have suitable or easy to optimise properties. The selected compounds showed cytotoxicity against breast adenocarcinoma, lung cancer cell lines, colon carcinoma, and T cells from acute leukaemia. Compound 2Ba5 exhibited the lowest toxicity, and derivative 4Db6 exhibited the most intense bioactivity. Molecular docking studies were also performed. The binding site of the 4Db6 compound in the glutamine synthetase structure was determined, with the D subunit and cluster 1 being the most promising. In conclusion, glutamic acid is an amino acid that can be manipulated very easily. Therefore, molecules derived from its structure have great potential to become innovative drugs, and further research on these will be conducted.

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E

Buckingham¹

1995

Dictionary of Natural Products

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Several 4-Substituted Glutamic Acid Derivatives and Small Peptides in Some Liliaceae Plants

Cited by 3 publications

References 25 publications

Preparation and Characterization of Four Stereoisomers of Monatin

Preparation and Characterization of Four Stereoisomers of Monatin

Identification of Some Glutamic Acid Derivatives with Biological Potential by Computational Methods

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