New sweetening agents. N'-formyl- and N'-acetylkynurenine

Finley, John W.; Friedman, Mendel

doi:10.1021/jf60185a014

Cited by 19 publications

(7 citation statements)

References 7 publications

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“…As the receptor distinguishes D-and L-amino acids, with a preference for D-amino acids, [32][33][34] the structural relationships between D-amino acids and other sweeteners and the structural features of D-amino acid derivatives that favor the activation of the sweet taste receptor have been studied using conformational analysis by crystallography, NMR analysis, and molecular modeling. However, it is still difficult to understand the receptor-bound conformations of the sweeteners, as the structural information on the ligands complexed with the receptor is limited.…”

Section: D-amino Acidsmentioning

confidence: 99%

Recent progress in the use of diaziridine-based sweetener derivatives to elucidate the chemoreception mechanism of the sweet taste receptor

2021

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Section: D-amino Acidsmentioning

confidence: 99%

Recent progress in the use of diaziridine-based sweetener derivatives to elucidate the chemoreception mechanism of the sweet taste receptor

2021

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“…13 Additionally, L-kynurenine has shown a sweetening power 50 times greater than sucrose; however, the D-enantiomer is tasteless and lacks biological activity. 14 The kynurenine pathway (KP) starts with the conversion of L-tryptophan (2) into N-formyl-L-kynurenine (3, Scheme 1) mediated by the enzymes indoleamine 2,3-dioxygenase (IDO) and tryptophan 2,3-dioxygenase (TDO). 1b,4…”

Section: Scheme 1 Metabolism Of L-tryptophan Via the Kynurenine Pathwmentioning

confidence: 99%

Synthesis of l-Kynurenine and Homo-l-Kynurenine via an Aza-Fries Rearrangement

2020

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l-Kynurenine, a non-proteinogenic amino acid, is the primary metabolite of tryptophan via the kynurenine pathway. Kynurenine is involved in a variety of biological processes occurring in the human body, notably in the central nervous system. Thus, the study of this molecule offers multiple opportunities for drug discovery; however, an essential prelude for biological studies is to secure the supply of kynurenine and analogues thereof. A simple synthetic procedure for the efficient preparation of enantiomerically pure l-kynurenine from l-aspartic acid and its implementation to prepare homo-l-kynurenine from l-glutamic acid is presented. The approach relies on a photochemical aza-Fries rearrangement of the corresponding acyl-aniline as the fundamental transformation.

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“…D-Cys but not N-acetyl-D-Cys lowered rat blood cyanide levels derived from acrylonitrile (Benz et al 1990). D-Cys is also reported to be involved in the detoxification and/or prevention of toxicities caused by cyanides (Huang et al 1998), the drug paracetamol (McLean et al 1989), and other drugs (Friedman 1973(Friedman , 1994Takahashi et al 1994). L-Cys-glutathione disulfide, but not the D-Cys analog, protected mice against acetaminophen-induced liver damage (Berkeley et al 2003).…”

Section: D-cysteinementioning

confidence: 99%

“…As discussed previously in the ''Nutritional utilization of D-amino acids or amino acid derivatives'', D-Trp may replace L-Trp in mice, but must be used at approximately 2.59 greater levels. Both D-Phe and D-Trp taste sweet (Finley and Friedman 1973;Friedman and Cuq 1988;Maehashi et al 2007;Manita et al 2006). D-Trp aldolase is involved in the biosynthesis of vitamin B6-dependent enzymes (Paiardini et al 2003).…”

Section: D-tryptophanmentioning

confidence: 99%

Nutritional and medicinal aspects of d-amino acids

2011

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This paper reviews and interprets a method for determining the nutritional value of D-amino acids, D-peptides, and amino acid derivatives using a growth assay in mice fed a synthetic all-amino acid diet. A large number of experiments were carried out in which a molar equivalent of the test compound replaced a nutritionally essential amino acid such as L-lysine (L-Lys), L-methionine (L-Met), L-phenylalanine (L-Phe), and L-tryptophan (L-Trp) as well as the semi-essential amino acids L-cysteine (L-Cys) and L-tyrosine (L-Tyr). The results show wide-ranging variations in the biological utilization of test substances. The method is generally applicable to the determination of the biological utilization and safety of any amino acid derivative as a potential nutritional source of the corresponding L-amino acid. Because the organism is forced to use the D-amino acid or amino acid derivative as the sole source of the essential or semi-essential amino acid being replaced, and because a free amino acid diet allows better control of composition, the use of all-amino-acid diets for such determinations may be preferable to protein-based diets. Also covered are brief summaries of the widely scattered literature on dietary and pharmacological aspects of 27 individual D-amino acids, D-peptides, and isomeric amino acid derivatives and suggested research needs in each of these areas. The described results provide a valuable record and resource for further progress on the multifaceted aspects of D-amino acids in food and biological samples.

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New sweetening agents. N'-formyl- and N'-acetylkynurenine

Cited by 19 publications

References 7 publications

Recent progress in the use of diaziridine-based sweetener derivatives to elucidate the chemoreception mechanism of the sweet taste receptor

Recent progress in the use of diaziridine-based sweetener derivatives to elucidate the chemoreception mechanism of the sweet taste receptor

Synthesis of l-Kynurenine and Homo-l-Kynurenine via an Aza-Fries Rearrangement

Nutritional and medicinal aspects of d-amino acids

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