Back to Search
Start Over
Biaryl amino acid templates in place of D-Pro-L-Pro in cyclic beta-hairpin cationic antimicrobial peptidomimetics.
- Source :
-
Organic & biomolecular chemistry [Org Biomol Chem] 2007 Oct 07; Vol. 5 (19), pp. 3100-5. Date of Electronic Publication: 2007 Aug 17. - Publication Year :
- 2007
-
Abstract
- The turn-forming D-Pro-L-Pro template has been frequently used to promote regular beta-hairpin conformations in cyclic protein epitope mimetics. Here the use of three isomeric biaryl templates has been studied as alternatives to D-Pro-L-Pro in the preparation of beta-hairpin peptidomimetics. The o,o'- o,m'- and m,m'-isomers of carboxymethyl- and aminomethyl-substituted biaryl templates have been incorporated into novel macrocyclic mimics of the naturally occurring cationic antimicrobial peptide protegrin I. The presence of the o-carboxymethyl-o'-aminomethyl-biaryl template within the macrocyclic peptide resulted in the appearance of slowly interconverting atropisomers. Although none of the resulting mimetics adopted stable beta-hairpin structures in aqueous solution, they all nevertheless retained a significant antimicrobial activity against Gram positive and Gram negative bacteria. These mimetics provide interesting starting points for an optimization program in the search for potent and novel antimicrobial compounds.
- Subjects :
- Antimicrobial Cationic Peptides chemistry
Chromatography, High Pressure Liquid
Circular Dichroism
Magnetic Resonance Spectroscopy
Peptides, Cyclic chemistry
Protein Conformation
Amino Acids chemistry
Antimicrobial Cationic Peptides chemical synthesis
Dipeptides chemistry
Peptides, Cyclic chemical synthesis
Subjects
Details
- Language :
- English
- ISSN :
- 1477-0520
- Volume :
- 5
- Issue :
- 19
- Database :
- MEDLINE
- Journal :
- Organic & biomolecular chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 17878968
- Full Text :
- https://doi.org/10.1039/b706370a