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. 2008 Nov 15;18(22):6007-11.
doi: 10.1016/j.bmcl.2008.09.019. Epub 2008 Sep 9.

Catalytic site-selective synthesis and evaluation of a series of erythromycin analogs

Chad A Lewis  1 , Janie Merkel, Scott J Miller
Affiliations

Catalytic site-selective synthesis and evaluation of a series of erythromycin analogs

Chad A Lewis et al. Bioorg Med Chem Lett. .

Abstract

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.

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Figures

Figure 1
Figure 1
Penicillin G and Erythromycin A (Ery A).
Figure 2
Figure 2
Catalyst-dependent functionalization of Ery A.
Figure 3
Figure 3
Ketalization of 2′,11 functionalized Ery A.
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