Cyclic peptides, Cyclic peptides-Synthesis, Solid-phase synthesis, Dimers, Cyclic peptide synthesis, Solid phase peptide synthesis, Fmoc SPPS
The rapid emergence of bacterial resistance to antibiotics has prompted an increased urgency in health sciences to investigate alternative methods of combating pathogens. A promising alternative can be found in nature as cationic antimicrobial peptides, which all organisms, from plants to humans, are known to produce. Novel antibiotics based on these cationic antimicrobial peptides have recently become a hot topic in research. Synthetically prepared peptides that disrupt ion gradients of the cell membrane through ionophore activity exhibit antimicrobial properties. We sought to synthesize an eight-residue cyclic peptide dimer, which was previously prepared by Ghadiri et al, composed of alternating D-MeN-Ala and L-Phe, and ultimately test it for ionophore activity. The synthesis was achieved through initial synthesis of its linear precursor via Fmoc solid phase peptide synthesis followed by in-solution cyclization. The successful synthesis was confirmed through mass spectrometry analysis.
Diaz, Virginia Marcela, "Synthesis of cyclo-[(L-Phe-D-[superscript me]N-Ala)₄-] dimer : a potential ion transporter" (2014). Honors Project, Smith College, Northampton, MA.
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