Christine M Crane1, Dale L Boger. 1. Department of Chemistry, The Scripps Research Institute, La Jolla, California 92037, USA.
Abstract
The synthesis and biological evaluation of a series of vancomycin aglycon analogues bearing alternative residue 1 N-methyl-D-amino acids are described. The analogues were prepared to define whether H-bonding d-amino acids could improve the affinity for the model ligands N,N'-Ac(2)-L-Lys-D-Ala-D-Ala (2) and N,N'-Ac(2)-L-Lys-D-Ala-D-Lac (3) and improve antimicrobial activity against vancomycin-sensitive or vancomycin-resistant bacteria. Additionally, a series of analogues with appended nucleophiles (hydrazines and amines) on the residue 1 D-amino acids are described that were examined for their ability to react with the C-terminal ester of 3, forming a covalent attachment of L-Lys-D-Ala to the natural product analogues.
The synthesis and biological evaluation of a series of vancomycin aglycon analogues bearing alternative residue 1 n class="Chemical">N-methyl-D-amino acids are described. The analogues were prepared to define whether H-bonding d-amino acids could improve the affinity for the model ligands N,N'-Ac(2)-L-Lys-D-Ala-D-Ala (2) and N,N'-Ac(2)-L-Lys-D-Ala-D-Lac (3) and improve antimicrobial activity against vancomycin-sensitive or vancomycin-resistant bacteria. Additionally, a series of analogues with appended nucleophiles (hydrazines and amines) on the residue 1 D-amino acids are described that were examined for their ability to react with the C-terminal ester of 3, forming a covalent attachment of L-Lys-D-Ala to the natural product analogues.
Authors: Jutta Wanner; Datong Tang; Casey C McComas; Brendan M Crowley; Wanlong Jiang; Jason Moss; Dale L Boger Journal: Bioorg Med Chem Lett Date: 2003-03-24 Impact factor: 2.823
Authors: Jian Xie; Akinori Okano; Joshua G Pierce; Robert C James; Simon Stamm; Christine M Crane; Dale L Boger Journal: J Am Chem Soc Date: 2012-01-06 Impact factor: 15.419