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Synthesis of adenine-based cationic and anionic amphiphiles

Prabhpreet Singh

Department of Chemistry, UGC Centre for Advanced Studies-II, Institution 1, Guru Nanak Dev University, Amritsar, India

 

E-mail: prabhpreet.chem@gndu.ac.in

Received: 8 October 2022  Accepted: 29 January 2023

Abstract:

Small molecule-based cationic and anionic amphiphiles could be potentially used as non-peptide antimicrobial mimics. In this paper, we have synthesized adenine-based butyloxycarbonyl (BOC)/tert-butyl protected derivatives (712) and deprotected (cationic and anionic) amphiphiles (16) which mimic extended poly ammonium and ethylenediamine tetraacetic acid type molecules, respectively, possessing different polyamines such as putrescine, spermidine and spermine as template. The newly synthesized compounds were characterized by 1H, 13C nuclear magnetic resonance, Mass, infra-red spectroscopies as well as by elemental analysis. These conjugates may be beneficial for non-covalent functionalization of nanomaterials, to target bacterial cell membranes and for molecular recognition of metal ions and biological anions in aqueous medium.

Graphical abstract

Synthesis and characterization of adenine-based BOC/tert-butyl protected derivatives (7–12) and cationic and anionic amphiphiles (1–6) have been reported.

Keywords: Nucleobase; Amphiphiles; Polyamines; Oligocarboxylic acid; Ammonium

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-023-02705-7

 

Chemical Papers 77 (6) 3305–3315 (2023)

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