Reactivity and degradation products of tryptophan in solution and proteins

Bellmaine, Stephanie; Schnellbaecher, Alisa; Zimmer, Aline

doi:10.1016/j.freeradbiomed.2020.09.002

Cited by 111 publications

(76 citation statements)

References 228 publications

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“…After 7 d, few valine-containing dipeptides were not yet formed, but these appear after 21 d. Similarly, most of the possible products are also formed in aqueous solution. However, tryptophan (W) shows low stability in solution and is susceptible to side reactions, especially in combination with metals or high temperatures 65 . After 7 d, this amino acid was rarely detected, and accordingly, dipeptide formation of W in aqueous solution occurred only very rarely.…”

Section: Resultsmentioning

confidence: 99%

From amino acid mixtures to peptides in liquid sulphur dioxide on early Earth

et al. 2021

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The formation of peptide bonds is one of the most important biochemical reaction steps. Without the development of structurally and catalytically active polymers, there would be no life on our planet. However, the formation of large, complex oligomer systems is prevented by the high thermodynamic barrier of peptide condensation in aqueous solution. Liquid sulphur dioxide proves to be a superior alternative for copper-catalyzed peptide condensations. Compared to water, amino acids are activated in sulphur dioxide, leading to the incorporation of all 20 proteinogenic amino acids into proteins. Strikingly, even extremely low initial reactant concentrations of only 50 mM are sufficient for extensive peptide formation, yielding up to 2.9% of dialanine in 7 days. The reactions carried out at room temperature and the successful use of the Hadean mineral covellite (CuS) as a catalyst, suggest a volcanic environment for the formation of the peptide world on early Earth.

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Section: Resultsmentioning

confidence: 99%

From amino acid mixtures to peptides in liquid sulphur dioxide on early Earth

et al. 2021

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“…In addition, the still-unexplored mechanism leading to the coloration of PTS, which-according to our analyses so far-is related but not limited to the composition of RONS and subsequent Trp modifications, may affect the molecular and cellular behavior of tumor cells. Next to the composition of RONS, the thermal and photochemical reactivity of the Trp metabolite Kyn into Kyn Yellow [46][47][48][49] may also be involved in the coloration of the PTS. Kyn Yellow is one of the 29 significant features identified in the HPLC-TOFMS analysis (Table S1).…”

Section: Discussionmentioning

confidence: 99%

Cold Atmospheric Plasma Changes the Amino Acid Composition of Solutions and Influences the Anti-Tumor Effect on Melanoma Cells

Arndt

Fadil

Dettmer

et al. 2021

IJMS

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Cold Atmospheric Plasma (CAP) is an ionized gas near room temperature. Its anti-tumor effect can be transmitted either by direct treatment or mediated by a plasma-treated solution (PTS), such as treated standard cell culture medium, which contains different amino acids, inorganic salts, vitamins and other substances. Despite extensive research, the active components in PTS and its molecular or cellular mechanisms are not yet fully understood. The purpose of this study was the measurement of the reactive species in PTS and their effect on tumor cells using different plasma modes and treatment durations. The PTS analysis yielded mode- and dose-dependent differences in the production of reactive oxygen and nitrogen species (RONS), and in the decomposition and modification of the amino acids Tyrosine (Tyr) and Tryptophan (Trp). The Trp metabolites Formylkynurenine (FKyn) and Kynurenine (Kyn) were produced in PTS with the 4 kHz (oxygen) mode, inducing apoptosis in Mel Im melanoma cells. Nitrated derivatives of Trp and Tyr were formed in the 8 kHz (nitrogen) mode, elevating the p16 mRNA expression and senescence-associated ß-Galactosidase staining. In conclusion, the plasma mode has a strong impact on the composition of the active components in PTS and affects its anti-tumor mechanism. These findings are of decisive importance for the development of plasma devices and the effectiveness of tumor treatment.

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“…The obtained salts in contact with air turn brown, which indicates a low chemical stability, which is related to the that tryptophan is highly susceptible to oxidative degradation and exposure to light. [37] Dissolving salt in water slows down this process by up to several weeks. The best method so far used by us to prevent the decomposition of the obtained salts were stored them in UV blocking vacuum desiccator over P 4 O 10 at 20°C.…”

Section: Synthesismentioning

confidence: 99%

Conversion of l‐Tryptophan Derivatives into Biologically Active Amino Acid Ionic Liquids

et al. 2021

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Natural auxins are a group of plant hormones that affect plant growth and development. The most common auxin is indole-3acetic acid (IAA), which is mainly synthesized from tryptophan. Since converting synthetic auxins into an ionic liquid increases their herbicidal activity, an attempt was made to synthesize new amino acid ionic liquids (AAILs) with l-tryptophanate anions. As a result of the synthesis, two homologous series, tetraalkylammonium l-tryptophanates and dialkyldimethylammonium l-tryptophanates, were obtained with yields exceeding 95 %. For the obtained AAILs, basic physicochemical properties (solubility in solvents of different polarity, thermal stability, phase changes, and surface activity) were determined, and whether the obtained salts act as growth stimulants for lettuce (Lactuca sativa L.) was evaluated. The transformation of l-tryptophan into AAILs improved the physicochemical properties and increased the auxin activity. In addition, the higher content of nutrients (micro-and macroelements) made lettuce a healthier food product.

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Reactivity and degradation products of tryptophan in solution and proteins

Cited by 111 publications

References 228 publications

From amino acid mixtures to peptides in liquid sulphur dioxide on early Earth

From amino acid mixtures to peptides in liquid sulphur dioxide on early Earth

Cold Atmospheric Plasma Changes the Amino Acid Composition of Solutions and Influences the Anti-Tumor Effect on Melanoma Cells

Conversion of l‐Tryptophan Derivatives into Biologically Active Amino Acid Ionic Liquids

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