Literature DB >> 15214775

Hydrophobic acetal and ketal derivatives of mannopeptimycin-alpha and desmethylhexahydromannopeptimycin-alpha: semisynthetic glycopeptides with potent activity against Gram-positive bacteria.

Russell G Dushin1, Ting-Zhong Wang, Phaik-Eng Sum, Haiyin He, Alan G Sutherland, Joseph S Ashcroft, Edmund I Graziani, Frank E Koehn, Patricia A Bradford, Peter J Petersen, Karen L Wheless, David How, Nancy Torres, Eileen B Lenoy, William J Weiss, Stanley A Lang, Steven J Projan, David M Shlaes, Tarek S Mansour.   

Abstract

The effect of introducing hydrophobic groups onto the disaccharide portion of the mannopeptimycins has been examined. Under acid-catalyzed conditions dimethyl acetals and ketals react on the terminal mannose of the disaccharide moiety of mannopeptimycin-alpha and the cyclohexylalanyl analogue 2. The preferentially formed monofunctionalized 4,6-acetals and -ketals display potent antibacterial activities against Gram-positive microorganisms, including MRSA, PRSP, and VRE pathogens.

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Year:  2004        PMID: 15214775     DOI: 10.1021/jm049765y

Source DB:  PubMed          Journal:  J Med Chem        ISSN: 0022-2623            Impact factor:   7.446


  6 in total

1.  Synthetic studies toward the mannopeptimycins: synthesis of orthogonally protected beta-hydroxyenduracididines.

Authors:  Kevin S Olivier; Michael S Van Nieuwenhze
Journal:  Org Lett       Date:  2010-04-16       Impact factor: 6.005

2.  Biosynthetic pathway for mannopeptimycins, lipoglycopeptide antibiotics active against drug-resistant gram-positive pathogens.

Authors:  Nathan A Magarvey; Brad Haltli; Min He; Michael Greenstein; John A Hucul
Journal:  Antimicrob Agents Chemother       Date:  2006-06       Impact factor: 5.191

3.  Synthetic studies toward mannopeptimycin-E: synthesis of the O-linked tyrosine 1,4-alpha,alpha-manno,manno-pyranosyl pyranoside.

Authors:  Ravula Satheesh Babu; Sanjeeva R Guppi; George A O'Doherty
Journal:  Org Lett       Date:  2006-04-13       Impact factor: 6.005

Review 4.  The evolving role of chemical synthesis in antibacterial drug discovery.

Authors:  Peter M Wright; Ian B Seiple; Andrew G Myers
Journal:  Angew Chem Int Ed Engl       Date:  2014-07-02       Impact factor: 15.336

5.  Synthesis of aza-analogues of the glycosylated tyrosine portion of mannopeptimycin-E.

Authors:  Sanjeeva R Guppi; George A O'Doherty
Journal:  J Org Chem       Date:  2007-05-26       Impact factor: 4.354

Review 6.  Enduracididine, a rare amino acid component of peptide antibiotics: Natural products and synthesis.

Authors:  Darcy J Atkinson; Briar J Naysmith; Daniel P Furkert; Margaret A Brimble
Journal:  Beilstein J Org Chem       Date:  2016-11-07       Impact factor: 2.883

  6 in total

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