Synthesis 2016; 48(24): 4443-4450
DOI: 10.1055/s-0035-1562727
paper
© Georg Thieme Verlag Stuttgart · New York

Multicomponent Domino Synthesis and Antibacterial Activity of Neomycin–Sugar Conjugates

Aurora Sganappaa, Maria Cristina Belluccib, Victor Nizetc, Yitzhak Tor*d, Alessandro Volonterio*a
  • aDepartment of Chemistry, Materials and Chemical Engineering ‘Giulio Natta’, Politecnico di Milano, via Mancinelli 7, 20141 Milano, Italy   Email: alessandro.volonterio@polimi.it
  • bDepartment of Food, Environmental and Nutritional Sciences, Università degli Studi di Milano, via Celoria 2, 20131 Milano, Italy
  • cDepartment of Pediatrics and Skaggs School of Pharmacy and Pharmaceutical Sciences, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA 92093-0358, USA
  • dDepartment of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA 92093-0358, USA   Email: ytor@ucsd.edu
Further Information

Publication History

Received: 21 May 2016

Accepted after revision: 27 June 2016

Publication Date:
16 August 2016 (eFirst)

This manuscript is dedicated to the memory of Vincenzo Volonterio

Abstract

An efficient multicomponent domino process that works under mild conditions was used for the synthesis of systematically modified neomycin–sugar conjugates. The final aminoglycoside derivatives were tested against methicillin-resistant Staphylococcus aureus, Klebsiella, and E. coli strains, and show activity comparable to the parent antibiotics. Such a strategy can impact multicomponent combinatorial syntheses of diverse biologically active conjugates.

Supporting Information