Modeling tyrosinase activity. Effect of ligand topology on aromatic ring hydroxylation: an overview.
Synthetic modeling of tyrosinase (o-phenol ring hydroxylation) has emerged as a novel class of successful biomimetic studies. It is a well-established fact that the reaction of dioxygen with copper(I) complexes of m-xylyl-based ligands generate putative copper-oxygen intermediate species such as side-on peroxo {CuII2(mu-O2)}2+ [in some cases bis-oxo {CuIII2(mu-O)2}2+ in equilibrium with isomeric side-on peroxo], due to oxygen activation. Electrophilic attack of such species brings about monooxygenase activity by incorporating one of the oxygens to m-xylyl ring of the ligand and the other oxygen is reduced to hydroxide ion. The goal of this review is to provide a concise overview of the present day knowledge in this field of research to emphasize the important role the designed ligands play in eliciting the desired tyrosinase-like chemistry.
De
Anindita
A
Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur 208 016, India.
Mandal
Sukanta
S
Mukherjee
Rabindranath
R
D001386:Azides / Q000737:chemistry; D032701:Biomimetics; D003300:Copper / Q000737:chemistry*; D006900:Hydroxylation; D008024:Ligands; D008956:Models, Chemical; D014442:Monophenol Monooxygenase / Q000737:chemistry* / Q000378:metabolism*; D012545:Schiff Bases / Q000737:chemistry; D013329:Structure-Activity Relationship; D014992:Xylenes / Q000737:chemistry
D001386:Azides; D008024:Ligands; D012545:Schiff Bases; D014992:Xylenes; D003300:Copper; D014442:Monophenol Monooxygenase; C031285:3-xylene