An enzyme-initiated domino hydroxylation-oxidation-carbo-Diels-Alder reaction cascade

Tetrahedron Letters

Volumn 37, Issue 22, 1996, Pages 3833-3836

  Müller, Gernot H ^a   Waldmann, Herbert ^a  

^a UNIVERSITY OF KARLSRUHE   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BICYCLIC 1,2 DIKETONE DERIVATIVE; KETONE DERIVATIVE; MONOPHENOL MONOOXYGENASE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; ENZYME MECHANISM; HYDROXYLATION; OXIDATION; REACTION ANALYSIS;

EID: 15844372442     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00727-7     Document Type: Article

References (18)

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3. b) R. A. Bunce, Tetrahedron 1995, 51, 13103 - 13159. Ho, T. Tandem Organic Reactions, Wiley-Interscience, 1992.
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14. H. Stephen, T. Stephen, Solubilities of Inorganic and Organic Compounds; Pergamon Press: Oxford, 1963; Vol 1 p 7.
15. 11 of the immobilized biocatalyst and 0.5 ml of phosphate buffer (pH 7, 0.05 M) is added. The mixture is gently shaken at ambient temperature until tic control indicates the complete disappearance of the phenol (1.5 to 6 d). The solution is decanted, the solvent is evaporated in vacuo and the remaining residue is purified by flash chromatography using hexane/ethyl acetate mixtures as eluents.
16. C. Grundmann, in Methoden der organischen Chemie (Houben Weyl) Band VII/3b (Ed.:E. Müller), Georg Thieme Verlag, Stuttgart 1979, pp 160 - 164.
17. 11 of enzymatic activity are obtained, which can be stored at -60°C for several months with only little loss of activity (after 50 days 90% and after 150 days 80% of the activity are retained).
18. 6. 1 unit of enzymatic activity is defined as the amount of enzyme which produces 1 μmol of dopachrome/min in a solution of L-dopa (10 mM in phosphate buffer (pH 6.0, 50 mM)). The reaction is followed with a spectrophotometer monitoring the increase in absorbance due to dopachrome formation at 475 nm (ε = 3600 / M cm ).