Laccase and Laccase‐Mediated Systems in the Synthesis of Organic Compounds

Abstract

Laccase, a blue multicopper oxidase, has recently received considerable attention because of its usefulness in oxidizing phenolic and non‐phenolic compounds, as well as its suitability for organic synthesis, environmental pollutant treatment, and other biotechnological applications. This review covers recent studies on the structural properties, occurrence, reaction mechnisms, redox mediators of laccases and their application in organic synthesis procedures, such as dimerization, polymerization, oxidation, and amination. We also present a brief discussion on laccase activity in non‐aqueous media. Given that the development of green protocols for the synthesis of pure compounds is one of the main goals of sustainable chemistry, the exploitation of laccases is expected to remain one of the most popular directions in future biocatalysis research.magnified image

Laccase‐Catalyzed Dimerization of Piceid, a Resveratrol Glucoside, and its Further Enzymatic Elaboration

“…As more and more laccases are becoming available,t heir synthetic exploitation is significantly growing, as documented by the numerous patents andl iterature reports. [12] In recent years our group has exploited these biocatalysts,i .e., for the selective oxidation of phenolic derivatives [13] and specifically of phenolic stilbenes. [6,14] Following ap reliminary optimization of the reaction parameters,a20 mM solution of piceid (3,1g dissolved in 140 mL of ab uffered solutionc ontaining 30% v/v MeOH to improve its solubility) waso xidized by the commercially available laccase from Trametes versicolor.T he reactionw as gently shaken at 25 8 8Cf or 2-3 hu ntil the starting material was completely oxidized.…”

Broadening the chemical scope of laccases: selective deprotection of N-benzyl groups

“…These oxidases can achieve mild oxidations in aqueous media and are compatible with different chemical oxidants, which has broadened their applicability in many (environmentally-friendly) processes. [23][24][25][26][27] While finding important roles in numerous oxidative transformations, only Rutjes and co-workers have performed a systematic study of these systems applied to the deprotection of amines when PMP group was employed. 22 Herein we have shown that this system can perfectly work for the removal of the benzyl moiety, widely utilized to protect amines and alcohols.…”

“…Herein we wish to report our latest results in the development of an efficient N-benzyl deprotection reaction taken advantage of the use of laccases (Scheme 1), [23][24][25][26][27] which are multi-copper enzymes found in a myriad of bacteria, fungi and plants. These oxidases reduce O2 into H2O at the expense of the oxidation of the corresponding substrate.…”

Laccase Immobilization on Poly(p-Phenylenediamine)/Fe3O4 Nanocomposite for Reactive Blue 19 Dye Removal

“…Laccase (p-diphenol: dioxygen oxidoreductase, EC 1.10.3.2) belongs to the family of copper-containing oxidases, which catalyze the 1-electron oxidation of a wide range of inorganic and organic substances, coupled with a 4-electron reduction of oxygen to water [1][2][3][4]. This enzyme is among the most studied redoxases and has been used successfully as a commercial industrial catalyst.…”

“…This enzyme is among the most studied redoxases and has been used successfully as a commercial industrial catalyst. Laccase (Lac) has shown many applications in biomedical, biotechnological, and environmental areas such as organic synthesis, wine cork making, teeth whitening, immunoassay analyte labeling, biofuel cells, and biosensors [4][5][6]. Moreover, Lac can also play a major role in bioremediation processes such as dye removal from wastewater [7,8].…”