Studies of para-quinomethane formation during the tyrosinase-catalyzed oxidation of 4-alkylcatechols

Journal article

UV-Vis spectroscopy, hplc-mass spectrometry and deuterium-labeling studies demonstrate that 4-alkyl-ortho-quinones cleanly rearrange to the isomeric 2-hydroxy-para-quinomethanes over a period of 10-20 minutes in aqueous buffer. These ortho-quinones are much more stable in organic solvents (CD3OH, CDCl3). Studies of the rate of rearrangement and of the introduction of pre-formed para-quinomethane to enzyme solution demonstrate that the quinomethanes, formed as secondary products, do not contribute to the inactivation of tyrosinase. ©ARKAT USA, Inc.

Authors: Land, E; Ramsden, C; Riley, P; Stratford, M

• Publication status: Published
• Journal: ARKIVOC
• Volume: 2008
• Issue: 2
• Pages: 258-267
• Publication date: 2008-01-01
• EISSN: 1551-7012
• ISSN: 1424-6376
• Language: English
• Keywords: oxidation; rearrangement; tyrosinase; para-quinomethanes; catechols; ortho-Quinones