Synthesis and biological evaluation of asymmetric gramicidin S analogues containing modified D-phenylalanine residues

Matthijs van der Knaap; Eefje Engels; Henk J Busscher; José M Otero; Antonio L Llamas-Saiz; Mark J van Raaij; Roos H Mars-Groenendijk; Daan Noort; Gijsbert A van der Marel; Herman S Overkleeft; Mark Overhand

doi:10.1016/j.bmc.2009.07.042

Synthesis and biological evaluation of asymmetric gramicidin S analogues containing modified D-phenylalanine residues

Bioorg Med Chem. 2009 Sep 1;17(17):6318-28. doi: 10.1016/j.bmc.2009.07.042. Epub 2009 Jul 25.

Authors

Matthijs van der Knaap¹, Eefje Engels, Henk J Busscher, José M Otero, Antonio L Llamas-Saiz, Mark J van Raaij, Roos H Mars-Groenendijk, Daan Noort, Gijsbert A van der Marel, Herman S Overkleeft, Mark Overhand

Affiliation

¹ Bio-Organic Synthesis, Leiden Institute of Chemistry, University of Leiden, Leiden, The Netherlands.

PMID: 19674904
DOI: 10.1016/j.bmc.2009.07.042

Abstract

The synthesis of new analogues of the cationic antimicrobial peptide gramicidin S, having a modified D-phenylalanine residue, their antibacterial properties against several gram positive and negative strains, as well as their hemolytic activity is reported.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Anti-Bacterial Agents / chemical synthesis*
Anti-Bacterial Agents / chemistry
Anti-Bacterial Agents / pharmacology
Erythrocytes / drug effects
Gramicidin / analogs & derivatives*
Gramicidin / chemical synthesis
Gramicidin / pharmacology
Hemolysis
Humans
Microbial Sensitivity Tests
Phenylalanine / chemistry*

Substances

Anti-Bacterial Agents
Gramicidin
Phenylalanine