Electrochemical synthesis of cysteinyldopas

Hansson, Christina

doi:10.1007/bf01948342

Cited by 3 publications

(3 citation statements)

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“…L-tyrosine, L-cysteine, GSH (reduced), TBP, TBC and mushroom tyrosinase were purchased from Sigma (St Louis, MO, USA). 5-S-Cysteinyldopa was synthesised as described previously (13). 4-tert-butylquinone (TBQ) was synthesised according to Teuber and Staiger (14).…”

Section: Chemicalsmentioning

confidence: 99%

“…1 H and 13 C nuclear magnetic resonance (NMR) spectra were recorded using a Bruker ARX500 spectrometer. Chemical shifts are reported in ppm relative to the solvent signal (CD 3 OD, 3.31 ppm in 1 H NMR and 49.15 ppm in 13 C NMR) and the coupling constants (J) in Hz. Mass spectra were recorded by a Jeol SX102 spectrometer with EI (compound 3) and FAB (compound 4) ionisation.…”

Section: Spectroscopy Studiesmentioning

confidence: 99%

“…13 C NMR (125 MHz) data for cys-TBC (3) and GS-TBC (4). The spectra were recorded in CD 3 OD; the chemical shifts are given in ppm relative to the solvent signal (49.15 ppm)…”

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confidence: 99%

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Tyrosinase‐Mediated Formation of a Reactive Quinone from the Depigmenting Agents, 4‐tert‐Butylphenol and 4‐tert‐Butylcatechol

Thörneby‐Andersson

Sterner

Hansson

2000

Pigment Cell Research

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Exposure of the skin to certain phenols or catechols such as 4-tert-butylphenol (TBP) and 4-tert-butylcatechol (TBC) may cause leukoderma. These substances are used in the polymer industry and numerous cases have been reported. Several theories of the mechanism for chemical leukoderma have been suggested. In the present study, TBP and TBC are shown to be oxidised by tyrosinase. The oxidation of TBC yields a quinone that is further investigated on its reactions with cysteine or glutathione (GSH). The products formed are isolated and identified by mass spectrometry and nuclear magnetic resonance as being 4-tert-butyl-6-S-cysteinylcatechol (cys-TBC) and 4-tert-butyl-6-S-glutathionylcatechol (GS-TBC). The reactive quinone is a strongly electrophilic substance that rapidly reacts with GSH. A depletion of the GSH defence system may give conditions where the quinone lives long enough to effect its toxic properties. The influence of the reactive tert-butylquinone on enzymatic activities is demonstrated by the inhibition of glyceraldehyde-3-phosphate dehydrogenase.

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Section: Chemicalsmentioning

confidence: 99%

Section: Spectroscopy Studiesmentioning

confidence: 99%

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Tyrosinase‐Mediated Formation of a Reactive Quinone from the Depigmenting Agents, 4‐tert‐Butylphenol and 4‐tert‐Butylcatechol

Thörneby‐Andersson

Sterner

Hansson

2000

Pigment Cell Research

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ChemInform Abstract: ELECTROCHEMICAL SYNTHESIS OF CYSTEINYLDOPAS

Hansson¹

1982

Chemischer Informationsdienst

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References

1992

Melanins and Melanogenesis

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Adenosine 3,5-monophosphate (cyclic AMP) as the mediator of melanocyte stimulating hormone (MSH) and norepinephrine on the frog skin. Endocrinology 84, 362-368. Acquaron, R. R., Rouge, F., and Aubert, C. (1981). Pheomelanin in albino negroes: Urinary excretion in Cameroonian subjects. In "Pigment Cell 1981: Phenotypic Expression in Pigment Cells" (M. Seiji, ed.), pp. 97-103. University of Tokyo Press, Tokyo. Agin, P. P., Desorochers, D. L., and Sayre, R. M. (1985). The relationship of immediate pigment darkening to minimal erythemal dose, skin and eye color. Photodermatol. 2, 288-294. Agius, C. (1985). The melano-macrophage centres of fish: A review. In "Fish Immunol ogy" (M.J. Manning and M. F. Tatner, eds.), pp. 85-105. Academic Press, New York. Agrup, G., Falck, B., Kennedy, B.-M., Rorsman, H., Rosengren, A.-M., and Rosengren, E. (1975). Formation of cysteinyldopa from glutathionedopa in melanoma. Acta Derm. Venereol. (Stockh.) 55, 1-3. Agrup, G., Hansson, C, Rorsman, H., Rosengren, A.-M., and Rosengren, E. (1978a). 5-5-Cysteinyldopa and trichochromes in red feathers. Acta Derm. Venereol. (Stockh.) 58, 269-282. Agrup, G., Lindbladh, C, Prota, G., Rorsman, H., Rosengren, A.-M., and Rosengren, E. (1978b). Trichochromes in the urine of melanoma patients./. Invest. Dermatol. 70, 90-91. Agrup, G., Hansson, C, Rorsman, H., Rosengren, E., and Tegner, E. (1983a). Methemoglobin catalyzed formation of dopa and 6-OH-dopa from tyrosine. Acta Derm. Venereol. (Stockh.) 63, 152-155. Agrup, G., Edholm, L.-E., Rorsman, H., and Rosengren, E. (1983b). Diastereoisomers of 5-5-cysteinyldopa. Acta Derm. Venereol. (Stockh.) 63, 59-61. Aime, S., and Crippa, P. R. (1988). 1 3 C solid-state cross polarization magic-angle-225 226 REFERENCES spinning nuclear magnetic resonance spectra of natural and synthetic melanins. Pigment Cell Res. 1, 355-357. Aime, S., Fasano, M., and Croombridge, C. (1990). Solid-state carbon-13 NMR char acterization of melanin free acids from biosynthetic and natural melanins. Gazz. Chim. Ital. 120, 663-664. Alena, F., Jimbow, K., and Ito, S. (1990). Melanocytotoxicity and antimelanoma effects of phenolic amine compounds in mice in vivo. Cancer Res. 50, 3743-3747. Allegri, G., Biasolo, M., Frison, G., Pelli, B., and Traldi, P. (1987). Collisional spectro scopy in structural characterization of melanins. 1. Pigment Cell Res. 1, 87-93. Allegri, G., Biasolo, M., Frison, G., Pelli, B., and Traldi, P. (1988). Collisional spectro scopy in structural characterization of melanins. 2. Laser desorption experiments on bio-and synthetic tryptophan melanins. Biomed. Environ. Mass. Spectrom. 15, 353-355. Allegri, G., Arban, R., Costa, C, Biasolo, M., Curcuruto, O., Pozzan, A, and Traldi, P. (1990). Fast atom bombardment mass spectrometry of dopamine melanogenesis intermediates. Pigment Cell Res. 3, 181-186. Allport, D. C, and Bu'Lock, J. D. (I960). Biosynthetic pathways in Daldinia concentrica. J. Chem. Soc. 654-662. Altschule, M. D., and Hegedus, Z. L. (1977). The importance of studying visceral melanins. Clin. Pharmacol. The...

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Electrochemical synthesis of cysteinyldopas

Cited by 3 publications

References 5 publications

Tyrosinase‐Mediated Formation of a Reactive Quinone from the Depigmenting Agents, 4‐tert‐Butylphenol and 4‐tert‐Butylcatechol

Tyrosinase‐Mediated Formation of a Reactive Quinone from the Depigmenting Agents, 4‐tert‐Butylphenol and 4‐tert‐Butylcatechol

ChemInform Abstract: ELECTROCHEMICAL SYNTHESIS OF CYSTEINYLDOPAS

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