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- W2000308999 abstract "During the oxidation of dihydrocaffeic acid catalyzed by mushroom tyrosinase, the corresponding quinone formed undergoes an unusual nonenzymatic intramolecular nucleophilic addition reaction yielding dihydroesculetin. This compound was further converted to the o-quinone which accumulated in the reaction mixture. Chemically synthesized dihydrocaffeiyl quinone also exhibited the same lactonization reaction. The product of the reaction was isolated and characterized by uv, ir, and NMR spectral studies. One of the minor products of enzymatic oxidation was identified to be caffeic acid. Since intramolecular cyclization dominated side chain desaturation, methyl ester of the parent acid was substituted in the tyrosinase reaction in order to suppress the cyclization route and monitor the side chain desaturation. Such studies readily generated methyl caffeate as the major product of tyrosinase-catalyzed oxidation of dihydrocaffeate methyl ester. The formation of this product was accounted for by a novel nonenzymatic route involving tautomerization of enzymatically generated dihydrocaffeiyl quinone to its quinone methide and subsequent aromatization of the latter. The above results indicate that (a) even weak nucleophiles such as carboxylate can react with quinones to form esters and (b) suitably substituted quinones undergo spontaneous quinone methide formation and rearrange further to yield α,β-unsaturated catechols as stable products. The significance of these reactions for sclerotization of insect cuticle is discussed." @default.
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- W2000308999 date "1989-12-01" @default.
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- W2000308999 title "Unusual, intramolecular cyclization and side chain desaturation of carboxyethyl-o-benzoquinone derivatives" @default.
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- W2000308999 doi "https://doi.org/10.1016/0045-2068(89)90045-x" @default.
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