Laccase-catalysed azide-alkyne cycloadditions: Synthesis of benzothiazole and benzimidazole fused 1,2,3-triazole derivatives by copper containing oxidoreductase enzymes

Abstract

A new approach for synthesizing triazole rings through the application of laccases, copper containing oxidoreductase enzymes is outlined. A series of benzothiazoles and benzimidazoles-functionalized alkynes were initially synthesized utilizing a biocatalysis laccase-based approach. The resultant alkynes were further treated with aryl azides in a 1,3-dipolar cycloaddition reaction facilitated by laccase enzymes to obtain 1,2,3-triazole-fused benzothiazoles and benzimidazoles.

Keywords:

• Biocatalysis
• click chemistry
• enzyme
• laccase

Acknowledgements

M.M.M. wishes to thank NRF funding and Wits staff for analytical support in NMR and mass spectroscopy. DB thanks Novozymes and the CSIR for enzymes.

Author contributions

M.M.M.: funding acquisition, conceptualization, investigation, writing original draft. A.V.: investigation. C.d.K.: supervision, writing – review and editing. D.B.: funding acquisition, conceptualization, supervision, writing – review and editing.

Disclosure statement

There are no conflicts to declare.