Literature DB >> 18819795

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

Chad A Lewis1, Janie Merkel, Scott J Miller.   

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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Year:  2008        PMID: 18819795      PMCID: PMC2669672          DOI: 10.1016/j.bmcl.2008.09.019

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN: 0960-894X            Impact factor:   2.823


  15 in total

Review 1.  Kinetic aspects of nonlinear effects in asymmetric catalysis.

Authors:  D G Blackmond
Journal:  Acc Chem Res       Date:  2000-06       Impact factor: 22.384

Review 2.  Modern methods to produce natural-product libraries.

Authors:  Ulrich Abel; Corinna Koch; Michael Speitling; Friedrich G Hansske
Journal:  Curr Opin Chem Biol       Date:  2002-08       Impact factor: 8.822

Review 3.  Genetic approaches to polyketide antibiotics. 1.

Authors:  Robert McDaniel; Mark Welch; C Richard Hutchinson
Journal:  Chem Rev       Date:  2005-02       Impact factor: 60.622

4.  Introduction: antibiotic resistance.

Authors:  Christopher Walsh; Gerard Wright
Journal:  Chem Rev       Date:  2005-02       Impact factor: 60.622

Review 5.  Translation and protein synthesis: macrolides.

Authors:  Leonard Katz; Gary W Ashley
Journal:  Chem Rev       Date:  2005-02       Impact factor: 60.622

6.  Site-selective derivatization and remodeling of erythromycin A by using simple peptide-based chiral catalysts.

Authors:  Chad A Lewis; Scott J Miller
Journal:  Angew Chem Int Ed Engl       Date:  2006-08-25       Impact factor: 15.336

Review 7.  Minimum inhibitory concentration (MIC) analysis and susceptibility testing of MRSA.

Authors:  German Bou
Journal:  Methods Mol Biol       Date:  2007

8.  Chemical modification of erythromycin antibiotics. 4. Structure-activity relationships of erythromycin esters.

Authors:  Y C Martin; P H Jones; T J Perun; W E Grundy; S Bell; R R Bower; N L Shipkowitz
Journal:  J Med Chem       Date:  1972-06       Impact factor: 7.446

9.  Chemical modifications of erythromycin antibiotics. 3. Synthesis of 4" and 11 esters of erythromycin A and B.

Authors:  P H Jones; T J Perun; E K Rowley; E J Baker
Journal:  J Med Chem       Date:  1972-06       Impact factor: 7.446

10.  Antibacterial activity of 2'-esters of erythromycin.

Authors:  P L Tardrew; J C Mao; D Kenney
Journal:  Appl Microbiol       Date:  1969-08
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  18 in total

1.  An approach to the site-selective deoxygenation of hydroxy groups based on catalytic phosphoramidite transfer.

Authors:  Peter A Jordan; Scott J Miller
Journal:  Angew Chem Int Ed Engl       Date:  2012-02-08       Impact factor: 15.336

Review 2.  Protecting-group-free synthesis as an opportunity for invention.

Authors:  Ian S Young; Phil S Baran
Journal:  Nat Chem       Date:  2009-06       Impact factor: 24.427

Review 3.  Asymmetric Iridium-Catalyzed C-C Coupling of Chiral Diols via Site-Selective Redox-Triggered Carbonyl Addition.

Authors:  Inji Shin; Michael J Krische
Journal:  Top Curr Chem       Date:  2016

4.  Catalytic site-selective thiocarbonylations and deoxygenations of vancomycin reveal hydroxyl-dependent conformational effects.

Authors:  Brandon S Fowler; Kai M Laemmerhold; Scott J Miller
Journal:  J Am Chem Soc       Date:  2012-05-23       Impact factor: 15.419

5.  Regiodivergent Glycosylations of 6-Deoxy-erythronolide B and Oleandomycin-Derived Macrolactones Enabled by Chiral Acid Catalysis.

Authors:  Jia-Hui Tay; Alonso J Argüelles; Matthew D DeMars; Paul M Zimmerman; David H Sherman; Pavel Nagorny
Journal:  J Am Chem Soc       Date:  2017-06-19       Impact factor: 15.419

6.  Diastereo- and Enantioselective Iridium Catalyzed Coupling of Vinyl Aziridines with Alcohols: Site-Selective Modification of Unprotected Diols and Synthesis of Substituted Piperidines.

Authors:  Gang Wang; Jana Franke; Chinh Q Ngo; Michael J Krische
Journal:  J Am Chem Soc       Date:  2015-06-15       Impact factor: 15.419

Review 7.  Applications of Nonenzymatic Catalysts to the Alteration of Natural Products.

Authors:  Christopher R Shugrue; Scott J Miller
Journal:  Chem Rev       Date:  2017-06-05       Impact factor: 60.622

8.  Site-selective bromination of vancomycin.

Authors:  Tejas P Pathak; Scott J Miller
Journal:  J Am Chem Soc       Date:  2012-03-30       Impact factor: 15.419

9.  Enantioselective sulfonylation reactions mediated by a tetrapeptide catalyst.

Authors:  Kristin Williams Fiori; Angela L A Puchlopek; Scott J Miller
Journal:  Nat Chem       Date:  2009-11       Impact factor: 24.427

10.  An approach to the site-selective diversification of apoptolidin A with peptide-based catalysts.

Authors:  Chad A Lewis; Kate E Longcore; Scott J Miller; Paul A Wender
Journal:  J Nat Prod       Date:  2009-10       Impact factor: 4.050

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