Literature DB >> 20871915

Structure-activity relationships of the phosphonate antibiotic dehydrophos.

Michael Kuemin1, Wilfred A van der Donk.   

Abstract

Synthetic derivatives of the phosphonate antibiotic dehydrophos were tested for antimicrobial activity. Both the phosphonate monomethyl ester and the vinyl phosphonate moiety proved to be important for bacteriocidal activity of the natural product.

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Year:  2010        PMID： 20871915      PMCID： PMC3109733          DOI： 10.1039/c0cc02958k

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  18 in total

1.  Characterization and structure of DhpI, a phosphonate O-methyltransferase involved in dehydrophos biosynthesis.

Authors:  Jin-Hee Lee; Brian Bae; Michael Kuemin; Benjamin T Circello; William W Metcalf; Satish K Nair; Wilfred A van der Donk
Journal:  Proc Natl Acad Sci U S A       Date:  2010-09-27       Impact factor: 11.205

2.  On the transport of tripeptide antibiotics in bacteria.

Authors:  H Diddens; H Zähner; E Kraas; W Göhring; G Jung
Journal:  Eur J Biochem       Date:  1976-06-15

3.  Phosphonopeptides as antibacterial agents: rationale, chemistry, and structure-activity relationships.

Authors:  F R Atherton; M J Hall; C H Hassall; R W Lambert; P S Ringrose
Journal:  Antimicrob Agents Chemother       Date:  1979-05       Impact factor: 5.191

4.  K-26, a novel inhibitor of angiotensin I converting enzyme produced by an actinomycete K-26.

Authors:  M Yamato; T Koguchi; R Okachi; K Yamada; K Nakayama; H Kase; A Karasawa; K Shuto
Journal:  J Antibiot (Tokyo)       Date:  1986-01       Impact factor: 2.649

5.  Time-dependent inhibition of Bacillus stearothermophilus alanine racemase by (1-aminoethyl)phosphonate isomers by isomerization to noncovalent slowly dissociating enzyme-(1-aminoethyl)phosphonate complexes.

Authors:  B Badet; K Inagaki; K Soda; C T Walsh
Journal:  Biochemistry       Date:  1986-06-03       Impact factor: 3.162

6.  Phosphonopeptides as substrates for peptide transport systems and peptidases of Escherichia coli.

Authors:  F R Atherton; M J Hall; C H Hassall; R W Lambert; W J Lloyd; A V Lord; P S Ringrose; D Westmacott
Journal:  Antimicrob Agents Chemother       Date:  1983-10       Impact factor: 5.191

7.  Phosphonamidates as transition-state analogue inhibitors of thermolysin.

Authors:  P A Bartlett; C K Marlowe
Journal:  Biochemistry       Date:  1983-09-27       Impact factor: 3.162

8.  Phosphonopeptides as antibacterial agents: mechanism of action of alaphosphin.

Authors:  F R Atherton; M J Hall; C H Hassall; R W Lambert; W J Lloyd; P S Ringrose
Journal:  Antimicrob Agents Chemother       Date:  1979-05       Impact factor: 5.191

9.  Antibacterial activity and mechanism of action of phosphonopeptides based on aminomethylphosphonic acid.

Authors:  F R Atherton; M J Hall; C H Hassall; R W Lambert; W J Lloyd; P S Ringrose; D Westmacott
Journal:  Antimicrob Agents Chemother       Date:  1982-10       Impact factor: 5.191

10.  Phosphonate analogues of pyruvate. Probes of substrate binding to pyruvate oxidase and other thiamin pyrophosphate-dependent decarboxylases.

Authors:  T A O'Brien; R Kluger; D C Pike; R B Gennis
Journal:  Biochim Biophys Acta       Date:  1980
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  7 in total

1.  Investigation of Amide Bond Formation during Dehydrophos Biosynthesis.

Authors:  Emily C Ulrich; Despina J Bougioukou; Wilfred A van der Donk
Journal:  ACS Chem Biol       Date:  2018-01-12       Impact factor: 5.100

2.  Stereochemistry of Hydride Transfer by Group III Alcohol Dehydrogenases Involved in Phosphonate Biosynthesis.

Authors:  Spencer C Peck; Seung Young Kim; Bradley S Evans; Wilfred A van der Donk
Journal:  Medchemcomm       Date:  2012-08       Impact factor: 3.597

3.  The antibiotic dehydrophos is converted to a toxic pyruvate analog by peptide bond cleavage in Salmonella enterica.

Authors:  Benjamin T Circello; Charles G Miller; Jin-Hee Lee; Wilfred A van der Donk; William W Metcalf
Journal:  Antimicrob Agents Chemother       Date:  2011-05-02       Impact factor: 5.191

4.  Revisiting the biosynthesis of dehydrophos reveals a tRNA-dependent pathway.

Authors:  Despina J Bougioukou; Subha Mukherjee; Wilfred A van der Donk
Journal:  Proc Natl Acad Sci U S A       Date:  2013-06-17       Impact factor: 11.205

Review 5.  Phosphonate biosynthesis and catabolism: a treasure trove of unusual enzymology.

Authors:  Spencer C Peck; Wilfred A van der Donk
Journal:  Curr Opin Chem Biol       Date:  2013-07-17       Impact factor: 8.822

Review 6.  Recent examples of α-ketoglutarate-dependent mononuclear non-haem iron enzymes in natural product biosyntheses.

Authors:  Shu-Shan Gao; Nathchar Naowarojna; Ronghai Cheng; Xueting Liu; Pinghua Liu
Journal:  Nat Prod Rep       Date:  2018-08-15       Impact factor: 13.423

7.  Synthesis of methylphosphonic acid by marine microbes: a source for methane in the aerobic ocean.

Authors:  William W Metcalf; Benjamin M Griffin; Robert M Cicchillo; Jiangtao Gao; Sarath Chandra Janga; Heather A Cooke; Benjamin T Circello; Bradley S Evans; Willm Martens-Habbena; David A Stahl; Wilfred A van der Donk
Journal:  Science       Date:  2012-08-31       Impact factor: 47.728
  7 in total

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