Enzymatic synthesis of Tinuvin

• Autor(es): Schroeder, M. ; Pereira, Luciana ; Rodríguez Couto, S. ; Erlacher, Angelika ; Schoening, K.-U. ; Paulo, Artur Cavaco ; Guebitz, G. M.
• Data: 2007
• Identificador Persistente: http://hdl.handle.net/1822/13562
• Origem: RepositóriUM - Universidade do Minho
• Assunto(s): Laccase; Oxidative coupling; Tinuvin; Trametes hirsuta; Biotransformation
• Tipo de Documento: Artigo
• Idioma: Inglês

Descrição

Coupling of 3-(3-tert-butyl-4-hydroxyphenyl) propionic acid methylester to 1H-benzotriazole using a laccase from Trametes hirsuta was studied. The potentially resulting coupling product Tinuvin 1130 is an important UV-absorber used in polymer based materials. Oxidation of the phenol by the laccase led to homomolecular coupling reactions while the laccase did not attack 1H-benzotriazole. Due to the homomolecular reaction of the phenol in the presence of laccase coupling of phenol and 1H-benzotriazole was only observed when 1H-benzotriazole was applied in four-fold molar excess. The reaction was monitored by UV/vis spectroscopy, TLC and MS (ion trap) analysis. Coupling of 1H-benzotriazole took place in ortho position according to the postulated mechanism.