Nitrite tryptophan reaction: evidence for an equilibrium between tryptophan and its nitrosated form

Mellet, Philippe; Noel, Patrick R.; Goutefongea, R.

doi:10.1021/jf00071a031

Cited by 13 publications

(15 citation statements)

References 4 publications

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“…In the present study the occurrence of a direct transnitrosation reaction between N-nitrosotryptophan derivatives and melatonin is unequivocally demonstrated by using both 15 N-NMR spectrometry for experiments performed in Me 2 SO and capillary-zone electrophoresis for reactions in aqueous solution at pH 7.4. Interestingly, the thermodynamical equilibrium of transfer of the nitroso-function from N-nitrosotryptophan derivatives to melatonin lies on the side of N-nitrosomelatonin (NOMela).…”

Section: Introductionmentioning

confidence: 55%

“…This solution contained the nitrosated endothelin-1 fragment 16-21 and was used for the experiment. 15…”

Section: Synthesis Of 15 N-nitrosoendothelin-1 Fragment 16-21mentioning

confidence: 99%

“…A mixture of N-acetyl-15 N-nitrosotryptophan and melatonin (Fig. 1A) slowly yielded 15 N-nitrosomelatonin ( Fig. 1B).…”

Section: Quantum-chemical Calculationsmentioning

confidence: 99%

“…At low pH values (pH 2–4) transnitrosation reactions between tryptophan derivatives are controversially discussed in the literature. In 1983 Ito et al [14] reported that N ‐nitrosotryptophan in lysozyme ( directly ) transnitrosates myoglobin at low pH but Mellet et al [15] rejected this conclusion because kinetic analyses demonstrated the intermediacy of HNO 2 as principal nitrosating compound and this view was validated by data of Bravo et al [16]. As the concentration of the intermediate HNO 2 (pK a = 3.1 [7]) is extremely low at physiological pH, an effective HNO 2 ‐dependent transnitrosation reaction between a N ‐nitrosotryptophan derivative and a N ‐terminal‐blocked tryptophan compound can be safely ignored.…”

Section: Introductionmentioning

confidence: 99%

“…the transfer of the nitroso-function from N-nitrosotryptophan derivatives to melatonin, is unequivocally demonstrated. In the lipophilic buffer dimethylsulfoxide reaction of N-acetyl-N-nitrosotryptophan (NANT) with melatonin was very slow (k ¼ 1.5 · 10 )6 /m/s), but reversible as shown by 15 N-NMR spectrometry. These measurements demonstrated also that the thermodynamical equilibrium lies on the side of N-nitrosomelatonin (NOMela).…”

Section: Introductionmentioning

confidence: 99%

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First insights into regiospecific transnitrosation reactions between tryptophan derivatives: melatonin as an effective target

Kirsch

Groot

2004

Journal of Pineal Research

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Melatonin, a derivative of the essential amino acid tryptophan, has been portrayed as a hormone, a tissue factor, an autocoid, a paracoid, and a vitamin with antioxidative capabilities. In the present study a novel reaction which cannot be attributed to any of these suggested features, i.e. the transfer of the nitroso-function from N-nitrosotryptophan derivatives to melatonin, is unequivocally demonstrated. In the lipophilic buffer dimethylsulfoxide reaction of N-acetyl-N-nitrosotryptophan (NANT) with melatonin was very slow (k = 1.5 x 10(-6)/m/s), but reversible as shown by 15N-NMR spectrometry. These measurements demonstrated also that the thermodynamical equilibrium lies on the side of N-nitrosomelatonin (NOMela). Quantum-chemical calculations performed with the third-generation density functional B97-2 additionally predicted that this is also the case in an aqueous environment. In fact, reaction of melatonin with either NANT or N-nitrosotryptophan located at the endothelin-1 fragment 16-21 yielded NOMela with a rate constant of 1.7 +/- 0.5/m/s as shown by capillary zone electrophoresis. Interestingly, the known reactive nitrogen oxide species scavenger, piperazine, did not inhibit the NANT-dependent nitrosation of melatonin, thus very strongly indicating a direct transnitrosation reaction. All of these capabilities are known from the reaction of S-nitrosothiols with thiolate anions and are believed to be highly important in the transport and targeting of nitric oxide.

show abstract

Section: Introductionmentioning

confidence: 55%

“…This solution contained the nitrosated endothelin-1 fragment 16-21 and was used for the experiment. 15…”

Section: Synthesis Of 15 N-nitrosoendothelin-1 Fragment 16-21mentioning

confidence: 99%

“…A mixture of N-acetyl-15 N-nitrosotryptophan and melatonin (Fig. 1A) slowly yielded 15 N-nitrosomelatonin ( Fig. 1B).…”

Section: Quantum-chemical Calculationsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

First insights into regiospecific transnitrosation reactions between tryptophan derivatives: melatonin as an effective target

Kirsch

Groot

2004

Journal of Pineal Research

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Proteins as Scavengers of Nitrite: Antimutagenic Implications

Kikugawa

Kato

1993

Antimutagenesis and Anticarcinogenesis Mechanisms III

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The effect of subchronic poisoning with potassium nitrate and sodium nitrite on the processes of intestinal absorption of D-xylose in rats

Grudziński

Szymański

1991

Arch. Environ. Contam. Toxicol.

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The intestinal transport of D-xylose was studied during subchronic poisoning of male Wistar rats with the oral administration of potassium nitrate and sodium nitrite. The metabolic parameters of small intestine mucosa were determined one hour after xylose administration, i.e., Na+/K(+)-ATPase, alkaline phosphatase, oxygen consumption, and lactic acid level. Nitrite reduced the absorption of xylose and decreased the activity of Na+/K(+)-ATPase and alkaline phosphatase. No effect of sodium nitrite was demonstrated on the aerobic metabolism of intestinal mucosa with an increased lactic acid level. Potassium nitrate did not effect the processes of intestinal absorption of xylose nor the metabolic parameters of small intestine mucosa.

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Nitrite tryptophan reaction: evidence for an equilibrium between tryptophan and its nitrosated form

Cited by 13 publications

References 4 publications

First insights into regiospecific transnitrosation reactions between tryptophan derivatives: melatonin as an effective target

First insights into regiospecific transnitrosation reactions between tryptophan derivatives: melatonin as an effective target

Proteins as Scavengers of Nitrite: Antimutagenic Implications

The effect of subchronic poisoning with potassium nitrate and sodium nitrite on the processes of intestinal absorption of D-xylose in rats

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