Synthesis of Nα-protected formamides from amino acids using MgO nano catalyst: Study of molecular docking and antibacterial activity

Mahadevaiah, Raghavendra; Lalithamba, Haraluru Shankaraiah; Shekarappa, Sharath; Hanumanaika, Rajanaika

doi:10.24200/sci.2017.4491

Synthesis of Nα-protected formamides from amino acids using MgO nano catalyst: Study of molecular docking and antibacterial activity

Document Type : Research Article

Authors

Raghavendra Mahadevaiah ¹

Haraluru Shankaraiah Lalithamba ¹

Sharath Shekarappa ²

Rajanaika Hanumanaika ³

¹ Department of Chemistry, Siddaganga Institute of Technology, Tumakuru - 572 103, Karnataka, India

² Department of PG Studies & Research in Biotechnology & Bioinformatics, Kuvempu University, Shankaraghatta - 577451, Shimoga, Karnataka, India

³ Department of Studies and Research in Environmental Science, Tumkur University, Tumakuru - 572 103, Karnataka, India

10.24200/sci.2017.4491

Abstract

Green synthesis of nano MgO particles and their application for the formylation of isocyanates of N-Fmoc/Cbz/Boc protected amino acids were reported. Nano magnesium oxide catalysed reaction of isocyanate with 96% formic acid has been established to obtain formamides. For this, the carboxyl group of protected amino acids were activated via mixed anhydride method and treated with NaN₃. The formed azides were converted into its isocyanates through Curtius rearrangement and treated with HCOOH and catalytic amount of nano MgO. The advantages of this method were remarkably simple and economically low cost nano metal oxide under milder reaction conditions. Most importantly, MgO can be easily separated and other basic impurities were removed through a simple work-up. This protocol showed high efficiency in catalysing this transformation in a greener fashion. The molecular docking study of the synthesized compounds was performed against the macromolecules sortase-A and glucosamine 6-phosphate synthase to understand the binding interactions. The results of in vitro antibacterial activities of the synthesized compounds were supported by docking analysis.

Keywords

Formamides

Nano MgO

Curtius rearrangement

Molecular docking

Antibacterial activity

Subjects