Literature DB >> 22568755

Silver(I)-promoted conversion of thioamides to amidines: divergent synthesis of a key series of vancomycin aglycon residue 4 amidines that clarify binding behavior to model ligands.

Akinori Okano1, Robert C James, Joshua G Pierce, Jian Xie, Dale L Boger.   

Abstract

Development of a general Ag(I)-promoted reaction for the conversion of thioamides to amidines is disclosed. This reaction was employed to prepare a key series of vancomycin aglycon residue 4 substituted amidines that were used to clarify their interaction with model ligands of peptidoglycan precursors and explore their resulting impact on antimicrobial properties.

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Year:  2012        PMID： 22568755      PMCID： PMC3365631          DOI： 10.1021/ja302808p

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  28 in total

1.  Partitioning the loss in vancomycin binding affinity for D-Ala-D-Lac into lost H-bond and repulsive lone pair contributions.

Authors:  Casey C McComas; Brendan M Crowley; Dale L Boger
Journal:  J Am Chem Soc       Date:  2003-08-06       Impact factor: 15.419

Review 2.  Structural modifications of glycopeptide antibiotics.

Authors:  A Malabarba; T I Nicas; R C Thompson
Journal:  Med Res Rev       Date:  1997-01       Impact factor: 12.944

Review 3.  Vancomycin resistance: decoding the molecular logic.

Authors:  C T Walsh
Journal:  Science       Date:  1993-07-16       Impact factor: 47.728

Review 4.  Vancomycin and related antibiotics.

Authors:  H R Perkins
Journal:  Pharmacol Ther       Date:  1982       Impact factor: 12.310

5.  Crystal structure of vancomycin.

Authors:  M Schäfer; T R Schneider; G M Sheldrick
Journal:  Structure       Date:  1996-12-15       Impact factor: 5.006

6.  Molecular basis for vancomycin resistance in Enterococcus faecium BM4147: biosynthesis of a depsipeptide peptidoglycan precursor by vancomycin resistance proteins VanH and VanA.

Authors:  T D Bugg; G D Wright; S Dutka-Malen; M Arthur; P Courvalin; C T Walsh
Journal:  Biochemistry       Date:  1991-10-29       Impact factor: 3.162

7.  Total synthesis of the ristocetin aglycon.

Authors:  Brendan M Crowley; Yoshiki Mori; Casey C McComas; Datong Tang; Dale L Boger
Journal:  J Am Chem Soc       Date:  2004-04-07       Impact factor: 15.419

8.  The specificity of combination between ristocetins and peptides related to bacterial cell wall mucopeptide precursors.

Authors:  M Nieto; H R Perkins
Journal:  Biochem J       Date:  1971-10       Impact factor: 3.857

9.  Modifications of the acyl-D-alanyl-D-alanine terminus affecting complex-formation with vancomycin.

Authors:  M Nieto; H R Perkins
Journal:  Biochem J       Date:  1971-08       Impact factor: 3.857

10.  Physicochemical properties of vancomycin and iodovancomycin and their complexes with diacetyl-L-lysyl-D-alanyl-D-alanine.

Authors:  M Nieto; H R Perkins
Journal:  Biochem J       Date:  1971-08       Impact factor: 3.857
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  22 in total

1.  Investigation into the functional impact of the vancomycin C-ring aryl chloride.

Authors:  Joseph R Pinchman; Dale L Boger
Journal:  Bioorg Med Chem Lett       Date:  2013-07-04       Impact factor: 2.823

Review 2.  Biosynthesis and Chemical Applications of Thioamides.

Authors:  Nilkamal Mahanta; D Miklos Szantai-Kis; E James Petersson; Douglas A Mitchell
Journal:  ACS Chem Biol       Date:  2019-01-30       Impact factor: 5.100

3.  N-Terminus Alkylation of Vancomycin: Ligand Binding Affinity, Antimicrobial Activity, and Site-Specific Nature of Quaternary Trimethylammonium Salt Modification.

Authors:  Zhi-Chen Wu; Nicholas A Isley; Dale L Boger
Journal:  ACS Infect Dis       Date:  2018-08-08       Impact factor: 5.084

4.  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

Review 5.  Biological, chemical, and biochemical strategies for modifying glycopeptide antibiotics.

Authors:  Edward Marschall; Max J Cryle; Julien Tailhades
Journal:  J Biol Chem       Date:  2019-10-31       Impact factor: 5.157

6.  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

7.  Peripheral modifications of [Ψ[CH2NH]Tpg4]vancomycin with added synergistic mechanisms of action provide durable and potent antibiotics.

Authors:  Akinori Okano; Nicholas A Isley; Dale L Boger
Journal:  Proc Natl Acad Sci U S A       Date:  2017-05-30       Impact factor: 11.205

Review 8.  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

9.  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

10.  Precursor-Directed Generation of Amidine Containing Ammosamide Analogs: Ammosamides E-P.

Authors:  Ende Pan; Nathaniel W Oswald; Aaron G Legako; Janie M Life; Bruce A Posner; John B Macmillan
Journal:  Chem Sci       Date:  2013-01       Impact factor: 9.825
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