RESUMEN

A practical gram-scale and high-yielding synthesis of the antimicrobial peptide gramicidin S is presented. An Fmoc-based solid-phase peptide synthesis protocol is employed for the generation of the linear decapeptide precursor, which is cyclized in solution to afford the target compound. The versatility of our method is demonstrated by the construction of eight gramicidin S analogues (15a-h) having nonproteinogenic sugar amino acid residues (4-7) incorporated in the turn regions.

Asunto(s)

Aminoácidos/síntesis química , Antibacterianos/síntesis química , Carbohidratos/síntesis química , Gramicidina/síntesis química , Aminoácidos/farmacología , Antibacterianos/farmacología , Bacillus cereus/efectos de los fármacos , Carbohidratos/farmacología , Enterococcus faecalis/efectos de los fármacos , Eritrocitos/efectos de los fármacos , Escherichia coli/efectos de los fármacos , Gramicidina/farmacología , Humanos , Pruebas de Sensibilidad Microbiana , Staphylococcus/efectos de los fármacos