A facile one-step synthesis of cysteinyldopas using mushroom tyrosinase
Specialia Pro Experimentis
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Summary
A convenient one-step procedure, based upon the tyrosinase co-oxidation of dopa and cysteine, is reported for the synthesis of 5-S-cysteinyldopa (I) in 74% yield. Secondary products of the reaction turned out to be 2-S-cysteinyldopa (II, 14%), 2,5-S, S-dicysteinyldopa (IV, 5%), and the hitherto unknown 6-S-cysteinyldopa (III, ∼1%).
Keywords
Cysteine Dopa Secondary Product Mushroom Tyrosinase Cysteinyldopas
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References
- 3.H. M. Thomson, Angew. Chem. Int. Ed.13, 305 (1974).CrossRefGoogle Scholar
- 4.G. Prota and R. H. Thomson, Endeavour35, 32 (1976).CrossRefPubMedGoogle Scholar
- 5.S. Ito and J. A. C. Nicol, Tetrahedron Lett.1975, 3287.Google Scholar
- 6.H. Rorsman, A-M. Rosengren and E. Rosengren, Yale J. Biol. Med.46, 516 (1973).PubMedGoogle Scholar
- 7.G. Agrup, P. Agrup, T. Anderson, B. Falck, J. A. Hausson, S. Jacobsson, H. Rorsman, A-M. Rosengren and E. Rosengren, Acta derm.-vener., Stockh.55, 337 (1975).Google Scholar
- 8.G. Prota, G. Scherillo and R. A. Nicolaus, Gazz. chim. ital.98, 495 (1968).Google Scholar
- 9.Evidence for this compound has been previously obtained by GLC-MS analysis (H. Rorsman and E. Rosengren, private communication).Google Scholar
- 10.S. Bouchilloux and A. Kodja, Bull. Soc. Chim. Biol.42, 69 (1960).Google Scholar
- 11.E. Fattorusso, L. Minale, S. De Stefano, G. Cimino and R. A. Nicolaus, Gazz. chim. ital.99, 969 (1969).Google Scholar
- 12.H. Rorsman, A-M. Rosengren and E. Rosengren, Acta derm.-vener., Stockh.52, 353 (1972).Google Scholar
- 13.A procedure has been described by Ito and Nicol5 for the isolation of 2,5-S,S-dicysteinyldopa in 8.5% yield.Google Scholar
- 14.The ratio does not take into account the amount of 2,5-S,S-dicysteinyldopa formed.Google Scholar
Copyright information
© Birkhäuser Verlag 1977