Catalytic site-selective synthesis and evaluation of a series of erythromycin analogs.
The generation of a series of analogs of erythromycin A (EryA, 2) is described. In this study, we compared two peptide-based catalysts-one originally identified from a catalyst screen (5) and its enantiomer (ent-5)-for the selective functionalization of EryA. The semi-synthetic analogs were subjected to MIC evaluation with two bacterial strains and compared to unfunctionalized EryA.
Lewis
Chad A
CA
Department of Chemistry, Yale University, 225 Prospect Street, New Haven, CT 06520-8107, USA.
Merkel
Janie
J
Miller
Scott J
SJ
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D020134:Catalytic Domain; D020650:Combinatorial Chemistry Techniques; D013293:Enterococcus faecalis / Q000187:drug effects*; D004917:Erythromycin / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D016106:Methicillin Resistance / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D010455:Peptides / Q000737:chemistry; D013237:Stereoisomerism; D013296:Streptococcus pneumoniae / Q000187:drug effects
D000900:Anti-Bacterial Agents; D010455:Peptides; D004917:Erythromycin