Literature DB >> 12643936

A new and improved method for deglycosidation of glycopeptide antibiotics exemplified with vancomycin, ristocetin, and ramoplanin.

Jutta Wanner1, Datong Tang, Casey C McComas, Brendan M Crowley, Wanlong Jiang, Jason Moss, Dale L Boger.   

Abstract

A general method for the deglycosidation of glycopeptide antibiotics has been developed. Treatment of vancomycin, ristocetin, and ramoplanin with anhydrous HF results in efficient cleavage of the sugars to provide the corresponding aglycons in high yield.

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Year:  2003        PMID： 12643936     DOI： 10.1016/s0960-894x(03)00051-9

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


  8 in total

1.  N-Terminal guanidine derivatives of teicoplanin antibiotics strongly active against glycopeptide resistant Enterococcus faecium.

Authors:  Zsolt Szűcs; Ilona Bereczki; Erzsébet Rőth; Márton Milánkovits; Eszter Ostorházi; Gyula Batta; Lajos Nagy; Zsuzsanna Dombrádi; Anikó Borbás; Pál Herczegh
Journal:  J Antibiot (Tokyo)       Date:  2020-05-15       Impact factor: 2.649

2.  Synthesis and evaluation of selected key methyl ether derivatives of vancomycin aglycon.

Authors:  Christine M Crane; Joshua G Pierce; Siegfried S F Leung; Julian Tirado-Rives; William L Jorgensen; Dale L Boger
Journal:  J Med Chem       Date:  2010-10-14       Impact factor: 7.446

3.  Total synthesis and structure of the ramoplanin A1 and A3 aglycons: two minor components of the ramoplanin complex.

Authors:  Dongwoo Shin; Yosup Rew; Dale L Boger
Journal:  Proc Natl Acad Sci U S A       Date:  2004-06-02       Impact factor: 11.205

4.  Synthesis and evaluation of vancomycin aglycon analogues that bear modifications in the N-terminal D-leucyl amino acid.

Authors:  Christine M Crane; Dale L Boger
Journal:  J Med Chem       Date:  2009-03-12       Impact factor: 7.446

5.  Precise Targeted Cleavage of a r(CUG) Repeat Expansion in Cells by Using a Small-Molecule-Deglycobleomycin Conjugate.

Authors:  Alicia J Angelbello; Mary E DeFeo; Christopher M Glinkerman; Dale L Boger; Matthew D Disney
Journal:  ACS Chem Biol       Date:  2020-03-18       Impact factor: 5.100

6.  Enzymatic glycosylation of vancomycin aglycon: completion of a total synthesis of vancomycin and N- and C-terminus substituent effects of the aglycon substrate.

Authors:  Atsushi Nakayama; Akinori Okano; Yiqing Feng; James C Collins; Karen C Collins; Christopher T Walsh; Dale L Boger
Journal:  Org Lett       Date:  2014-06-23       Impact factor: 6.005

7.  Semisynthetic teicoplanin derivatives with dual antimicrobial activity against SARS-CoV-2 and multiresistant bacteria.

Authors:  Ilona Bereczki; Vladimir Vimberg; Eszter Lőrincz; Henrietta Papp; Lajos Nagy; Sándor Kéki; Gyula Batta; Ana Mitrović; Janko Kos; Áron Zsigmond; István Hajdú; Zsolt Lőrincz; Dávid Bajusz; László Petri; Jan Hodek; Ferenc Jakab; György M Keserű; Jan Weber; Lieve Naesens; Pál Herczegh; Anikó Borbás
Journal:  Sci Rep       Date:  2022-09-26       Impact factor: 4.996

8.  Anti-influenza virus activity and structure-activity relationship of aglycoristocetin derivatives with cyclobutenedione carrying hydrophobic chains.

Authors:  Lieve Naesens; Evelien Vanderlinden; Erzsébet Roth; József Jeko; Graciela Andrei; Robert Snoeck; Christophe Pannecouque; Eszter Illyés; Gyula Batta; Pál Herczegh; Ferenc Sztaricskai
Journal:  Antiviral Res       Date:  2009-02-05       Impact factor: 5.970
  8 in total

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