Literature DB >> 8698642

Reductive alkylation of glycopeptide antibiotics: synthesis and antibacterial activity.

R D Cooper1, N J Snyder, M J Zweifel, M A Staszak, S C Wilkie, T I Nicas, D L Mullen, T F Butler, M J Rodriguez, B E Huff, R C Thompson.   

Abstract

Reductive alkylation of the A82846 family of glycopeptide antibiotics has the potential of producing seven products. N-Alkylation of the disaccharide amino function can be accomplished selectively, and offers the greatest increase in antibacterial activity. Products resulting from N-alkylation of LY264826 (A82846B) provide the most potent derivatives as compared to other members of this class of antibiotics. Two of these derivatives, LY307599 and LY333328 are approximately 500 times more active than vancomycin against vancomycin-resistant enterococci.

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Year:  1996        PMID: 8698642     DOI: 10.7164/antibiotics.49.575

Source DB:  PubMed          Journal:  J Antibiot (Tokyo)        ISSN: 0021-8820            Impact factor:   2.649


  45 in total

Review 1.  Vancomycin-resistant enterococci.

Authors:  Y Cetinkaya; P Falk; C G Mayhall
Journal:  Clin Microbiol Rev       Date:  2000-10       Impact factor: 26.132

2.  A stepwise dechlorination/cross-coupling strategy to diversify the vancomycin 'in-chloride'.

Authors:  Tyler J Wadzinski; Katherine D Gea; Scott J Miller
Journal:  Bioorg Med Chem Lett       Date:  2015-12-11       Impact factor: 2.823

3.  Telavancin, a multifunctional lipoglycopeptide, disrupts both cell wall synthesis and cell membrane integrity in methicillin-resistant Staphylococcus aureus.

Authors:  Deborah L Higgins; Ray Chang; Dmitri V Debabov; Joey Leung; Terry Wu; Kevin M Krause; Erik Sandvik; Jeffrey M Hubbard; Koné Kaniga; Donald E Schmidt; Qiufeng Gao; Robert T Cass; Dane E Karr; Bret M Benton; Patrick P Humphrey
Journal:  Antimicrob Agents Chemother       Date:  2005-03       Impact factor: 5.191

4.  The Carboxyl Terminus of Eremomycin Facilitates Binding to the Non-d-Ala-d-Ala Segment of the Peptidoglycan Pentapeptide Stem.

Authors:  James Chang; Hongyu Zhou; Maria Preobrazhenskaya; Peng Tao; Sung Joon Kim
Journal:  Biochemistry       Date:  2016-06-07       Impact factor: 3.162

Review 5.  Total Syntheses of Vancomycin-Related Glycopeptide Antibiotics and Key Analogues.

Authors:  Akinori Okano; Nicholas A Isley; Dale L Boger
Journal:  Chem Rev       Date:  2017-04-24       Impact factor: 60.622

6.  Hexapeptide derivatives of glycopeptide antibiotics: tools for mechanism of action studies.

Authors:  Norris E Allen; Deborah L LeTourneau; Joe N Hobbs; Richard C Thompson
Journal:  Antimicrob Agents Chemother       Date:  2002-08       Impact factor: 5.191

7.  Probing the role of the vancomycin e-ring aryl chloride: selective divergent synthesis and evaluation of alternatively substituted E-ring analogues.

Authors:  Joseph R Pinchman; Dale L Boger
Journal:  J Med Chem       Date:  2013-05-13       Impact factor: 7.446

Review 8.  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

Review 9.  Glycopeptide antibiotics: from conventional molecules to new derivatives.

Authors:  Françoise Van Bambeke; Yves Van Laethem; Patrice Courvalin; Paul M Tulkens
Journal:  Drugs       Date:  2004       Impact factor: 9.546

10.  Vancomycin analogs: Seeking improved binding of d-Ala-d-Ala and d-Ala-d-Lac peptides by side-chain and backbone modifications.

Authors:  Siegfried S F Leung; Julian Tirado-Rives; William L Jorgensen
Journal:  Bioorg Med Chem       Date:  2009-07-10       Impact factor: 3.641

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