Enzymatic synthesis of Tinuvin

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 l...

Full description

Bibliographic Details
Main Author: Schroeder, M. (author)
Other Authors: Pereira, Luciana (author), Rodríguez Couto, S. (author), Erlacher, Angelika (author), Schoening, K.-U. (author), Paulo, Artur Cavaco (author), Guebitz, G. M. (author)
Format: article
Language:eng
Published: 2007
Subjects:
Laccase
Oxidative coupling
Tinuvin
Trametes hirsuta
Biotransformation
Science & Technology
Online Access:http://hdl.handle.net/1822/13562
Country:Portugal
Oai:oai:repositorium.sdum.uminho.pt:1822/13562
Description
Summary: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.

Similar Items