TITLE

Biocatalytic oxidation of 4-vinylphenol by Nocardia

AUTHOR(S)

Lee, Kyung-Seon; Rosazza, John PN

PUB. DATE

June 2002

SOURCE

Canadian Journal of Chemistry;Jun2002, Vol. 80 Issue 6, p582

SOURCE TYPE

Academic Journal

DOC. TYPE

Article

ABSTRACT

Nocardia species NRRL 5646 stereospecifically hydrates 4-vinylphenol (15) to S-1-(4'-hydroxyphenyl)ethanol (17), and further oxidizes 17 to 4'-hydroxyacetophenone (18). Labeled metabolites 17 and 18 obtained from incubations in D[sub 2] O and H[sub 2] [sup 18] O support initial enzymatic tautomerization of 15 to a reactive quinone methide (16), which adds water in the first reaction. Commitment to catalysis is high in the hydration reaction, while the alcohol dehydrogenation reaction appears to be reversible. The stereochemical features of water addition, alcohol oxidations, and ketone reductions with growing culture biocatalysis were established by chiral HPLC. Alcohol oxidations or ketone reductions in 12 000 � g supernatants preferentially require NADP[sup +] �NADPH,H[sup +] as co-factors. The alcohol dehydrogenase has broad substrate specificity, favoring the oxidation of primary alkanols and 4-hydroxybenzyl alcohols.Key words : 4-vinylphenol, Nocardia sp., enantiospecific hydration, 1-(4'-hydroxyphenyl)ethanol, 4'-hydroxyacetophenoneL'esp�ce Nocardia NRRL 5446 hydrate st�r�osp�cifiquement le 4-vinylph�nol (15) en S-1-(4'-hydroxyph�nyl)�thanol (17) qu'il oxyde aussi en 4'-hydroxyac�toph�none (18). Les m�tabolites 17 et 18 marqu�s obtenus par incubation dans D[sub 2] O et H[sub 2] [sup 18] O sont en accord avec un m�canisme impliquant une tautom�risation enzymatique initiale de 15 en une m�thoquinone r�active (16) qui fixe de l'eau dans la premi�re �tape de la r�action. Dans la r�action d'hydratation, le degr� de catalyse est �lev� alors que la r�action de d�shydrog�nation de l'alcool semble r�versible. Faisant appel � la CLHP chirale, on a d�termin� les caract�ristiques st�r�ochimiques de l'addition d'eau, des oxydations de l'alcool et des r�ductions de c�tone par la catalyse de cultures en croissance. Les oxydations d'alcool ou r�ductions de c�tones dans des liquides surnageant 12,000 � g requi�rent le coupe NADP[sup +] �NADPH,H[sup +] comme cofacteurs. La d�shydrog�nase de l'alcool poss�de une grande sp�cificit� par rapport au substrat qui favorise l'oxydation d'alcools primaires et d'alcools 4-hydroxybenzyliques.Mots cl�s : 4-vinylph�nol, Nocardia sp., hydratation sp�cifique, 1-(4'-hydroxyph�nyl) �thanol, 4'-hydroxyac�toph�none.[Traduit par la R�daction]

ACCESSION #

10586793

Tags: ENANTIOMERS;  OXIDATION;  HYDRATION;  NOCARDIA

 

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