Literature DB >> 20232818

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

Kevin S Olivier1, Michael S Van Nieuwenhze.   

Abstract

The asymmetric synthesis of the nonproteinogenic amino acids (2S,3S,4'S)-beta-hydroxyenduracididine 3 and (2R,3S,4'S)-beta-hydroxyenduracididine 4 in orthogonally protected form in 15 total steps from Garner's aldehyde is reported. The former and N-glycosylated form of the latter are found in the glycopeptide antibiotic mannopeptimycin.

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Year:  2010        PMID： 20232818      PMCID： PMC2871400          DOI： 10.1021/ol100219a

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  11 in total

1.  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

Review 2.  The VISA/GISA problem: therapeutic implications.

Authors:  J Liñares
Journal:  Clin Microbiol Infect       Date:  2001       Impact factor: 8.067

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.  Mannopeptimycins, a novel class of glycopeptide antibiotics active against gram-positive bacteria.

Authors:  Haiyin He
Journal:  Appl Microbiol Biotechnol       Date:  2005-02-09       Impact factor: 4.813

5.  Mannopeptimycins, novel antibacterial glycopeptides from Streptomyces hygroscopicus, LL-AC98.

Authors:  Haiyin He; R Thomas Williamson; Bo Shen; Edmund I Graziani; Hui Y Yang; Subas M Sakya; Pete J Petersen; Guy T Carter
Journal:  J Am Chem Soc       Date:  2002-08-21       Impact factor: 15.419

6.  In vivo efficacy and pharmacokinetics of AC98-6446, a novel cyclic glycopeptide, in experimental infection models.

Authors:  William J Weiss; Timothy Murphy; Eileen Lenoy; Mairead Young
Journal:  Antimicrob Agents Chemother       Date:  2004-05       Impact factor: 5.191

7.  Invasive methicillin-resistant Staphylococcus aureus infections in the United States.

Authors:  R Monina Klevens; Melissa A Morrison; Joelle Nadle; Susan Petit; Ken Gershman; Susan Ray; Lee H Harrison; Ruth Lynfield; Ghinwa Dumyati; John M Townes; Allen S Craig; Elizabeth R Zell; Gregory E Fosheim; Linda K McDougal; Roberta B Carey; Scott K Fridkin
Journal:  JAMA       Date:  2007-10-17       Impact factor: 56.272

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

Authors:  Russell G Dushin; 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
Journal:  J Med Chem       Date:  2004-07-01       Impact factor: 7.446

9.  Comparative in vitro activities of AC98-6446, a novel semisynthetic glycopeptide derivative of the natural product mannopeptimycin alpha, and other antimicrobial agents against gram-positive clinical isolates.

Authors:  Peter J Petersen; T Z Wang; Russell G Dushin; Patricia A Bradford
Journal:  Antimicrob Agents Chemother       Date:  2004-03       Impact factor: 5.191

10.  Mechanism of action of the mannopeptimycins, a novel class of glycopeptide antibiotics active against vancomycin-resistant gram-positive bacteria.

Authors:  Alexey Ruzin; Guy Singh; Anatoly Severin; Youjun Yang; Russell G Dushin; Alan G Sutherland; Albert Minnick; Michael Greenstein; Michael K May; David M Shlaes; Patricia A Bradford
Journal:  Antimicrob Agents Chemother       Date:  2004-03       Impact factor: 5.191
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  3 in total

1.  Structural and functional characterization of MppR, an enduracididine biosynthetic enzyme from streptomyces hygroscopicus: functional diversity in the acetoacetate decarboxylase-like superfamily.

Authors:  A Maxwell Burroughs; Robert W Hoppe; Neal C Goebel; Bilal H Sayyed; Tyler J Voegtline; Alan W Schwabacher; T Mark Zabriskie; Nicholas R Silvaggi
Journal:  Biochemistry       Date:  2013-06-21       Impact factor: 3.162

2.  Aminodiols via stereocontrolled oxidation of methyleneaziridines.

Authors:  Jared W Rigoli; Ilia A Guzei; Jennifer M Schomaker
Journal:  Org Lett       Date:  2014-03-11       Impact factor: 6.005

Review 3.  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
  3 in total

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