Literature DB >> 17441081

Vancomycin analogues containing monosaccharides exhibit improved antibiotic activity: a combined one-pot enzymatic glycosylation and chemical diversification strategy.

Desiree A Thayer1, Chi-Huey Wong.   

Abstract

Many natural products contain carbohydrate moieties that contribute to their biological activity. Manipulation of the carbohydrate domain of natural products through multiple glycosylations to identify new derivatives with novel biological activities has been a difficult and impractical process. We report a practical one-pot enzymatic approach with regeneration of cosubstrates to synthesize analogues of vancomycin that contain an N-alkyl glucosamine, which exhibited marked improvement in antibiotic activity against a vancomycin-resistant strain of Enterococcus.

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Year:  2006        PMID： 17441081     DOI： 10.1002/asia.200600084

Source DB:  PubMed          Journal:  Chem Asian J        ISSN： 1861-471X


  9 in total

1.  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

2.  Total syntheses and initial evaluation of [Ψ[C(═S)NH]Tpg⁴]vancomycin, [Ψ[C(═NH)NH]Tpg⁴]vancomycin, [Ψ[CH₂NH]Tpg⁴]vancomycin, and their (4-chlorobiphenyl)methyl derivatives: synergistic binding pocket and peripheral modifications for the glycopeptide antibiotics.

Authors:  Akinori Okano; Atsushi Nakayama; Kejia Wu; Erick A Lindsey; Alex W Schammel; Yiqing Feng; Karen C Collins; Dale L Boger
Journal:  J Am Chem Soc       Date:  2015-03-09       Impact factor: 15.419

3.  Maxamycins: Durable Antibiotics Derived by Rational Redesign of Vancomycin.

Authors:  Zhi-Chen Wu; Dale L Boger
Journal:  Acc Chem Res       Date:  2020-11-02       Impact factor: 22.384

Review 4.  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

5.  Tackling vancomycin-resistant bacteria with 'lipophilic-vancomycin-carbohydrate conjugates'.

Authors:  Venkateswarlu Yarlagadda; Mohini M Konai; Goutham B Manjunath; Chandradhish Ghosh; Jayanta Haldar
Journal:  J Antibiot (Tokyo)       Date:  2014-10-29       Impact factor: 2.649

Review 6.  Teicoplanin biosynthesis: unraveling the interplay of structural, regulatory, and resistance genes.

Authors:  Oleksandr Yushchuk; Bohdan Ostash; Andrew W Truman; Flavia Marinelli; Victor Fedorenko
Journal:  Appl Microbiol Biotechnol       Date:  2020-02-19       Impact factor: 5.560

Review 7.  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

8.  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

9.  Total synthesis of [Ψ[C(═NH)NH]Tpg(4)]vancomycin and its (4-chlorobiphenyl)methyl derivative: impact of peripheral modifications on vancomycin analogues redesigned for dual D-Ala-D-Ala and D-Ala-D-Lac binding.

Authors:  Akinori Okano; Atsushi Nakayama; Alex W Schammel; Dale L Boger
Journal:  J Am Chem Soc       Date:  2014-09-16       Impact factor: 15.419
  9 in total

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