Gamma-aapeptides with potent and broad-spectrum antimicrobial activity

A γ-AApeptide prepared by a process comprising the steps of:

• reacting an Fmoc protected amino aldehyde comprising:
• wherein R1 is a straight or branched chain C1 to C10 alkyl group, —CH2—CH2—S—CH3;
• a —(CH2)1-5-aryl group, or an —(CH2)1-5-heteroaryl group, and wherein the alkyl group, the aryl group or the heteroaryl group can be substituted or unsubstituted, with glycine benzyl ester comprising:
• to form a secondary amine comprising:
• reacting
• with a substituted or unsubstituted aryl, substituted or unsubstituted 5-membered heterocyclic ring of which one to four member(s) may be heteroatoms, γ-Boc-amino butyric acid, di-Boc-guanidinopropionic acid, mono-allyl succinate or substituted or unsubstituted alkanoic acid followed by hydrogenation to form γ-AApeptide building blocks comprising:
• wherein R2 is substituted or unsubstituted aryl, substituted or unsubstituted 5-membered heterocyclic ring of which one to four member(s) may be heteroatoms, amino-propyl, allyl-propyl, or substituted or unsubstituted alkyl;
• attaching a first γ-AApeptide building block to a solid support;
• coupling the first γ-AApeptide building block with a second γ-AApeptide building block;
• repeating the coupling step to form the γ-AApeptide attached to the solid support;
• and
• cleaving the γ-AApeptide attached to the solid support from the solid support to form the γ-AApeptide.