Literature DB >> 20047918

Antibacterial activity of N-pentylpantothenamide is due to inhibition of coenzyme a synthesis.

Jacob Thomas1, John E Cronan.   

Abstract

Growth inhibition by the pantothenate analog N-pentylpantothenamide (N5-Pan) has been attributed to the accumulation of acyl carrier protein carrying a prosthetic group modified by incorporation of N5-Pan. This was attributed to an inability of the AcpH acyl carrier protein phosphodiesterase to cleave the N5-Pan-modified prosthetic group from the protein moiety. We report that AcpH readily removes the N5-Pan-modified prosthetic group both in vivo and in vitro and show that N5-Pan blocks coenzyme A synthesis.

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Year:  2010        PMID: 20047918      PMCID: PMC2826004          DOI: 10.1128/AAC.01473-09

Source DB:  PubMed          Journal:  Antimicrob Agents Chemother        ISSN: 0066-4804            Impact factor:   5.191


  23 in total

1.  Holo-(acyl carrier protein) synthase and phosphopantetheinyl transfer in Escherichia coli.

Authors:  R S Flugel; Y Hwangbo; R H Lambalot; J E Cronan; C T Walsh
Journal:  J Biol Chem       Date:  2000-01-14       Impact factor: 5.157

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Journal:  J Biol Chem       Date:  1967-04-25       Impact factor: 5.157

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Authors:  G Clifton; S R Bryant; C G Skinner
Journal:  Arch Biochem Biophys       Date:  1970-04       Impact factor: 4.013

4.  Acyl carrier protein from Escherichia coli.

Authors:  C O Rock; J E Cronan
Journal:  Methods Enzymol       Date:  1981       Impact factor: 1.600

5.  The antibiotic activity of N-pentylpantothenamide results from its conversion to ethyldethia-coenzyme a, a coenzyme a antimetabolite.

Authors:  Erick Strauss; Tadhg P Begley
Journal:  J Biol Chem       Date:  2002-10-07       Impact factor: 5.157

6.  The structure of the pantothenate kinase.ADP.pantothenate ternary complex reveals the relationship between the binding sites for substrate, allosteric regulator, and antimetabolites.

Authors:  Robert A Ivey; Yong-Mei Zhang; Kristopher G Virga; Kirk Hevener; Richard E Lee; Charles O Rock; Suzanne Jackowski; Hee-Won Park
Journal:  J Biol Chem       Date:  2004-05-10       Impact factor: 5.157

7.  Regulation of coenzyme A biosynthesis.

Authors:  S Jackowski; C O Rock
Journal:  J Bacteriol       Date:  1981-12       Impact factor: 3.490

8.  Beta-alanine synthesis in Escherichia coli.

Authors:  J E Cronan
Journal:  J Bacteriol       Date:  1980-03       Impact factor: 3.490

9.  Purification and properties of L-Aspartate-alpha-decarboxylase, an enzyme that catalyzes the formation of beta-alanine in Escherichia coli.

Authors:  J M Williamson; G M Brown
Journal:  J Biol Chem       Date:  1979-08-25       Impact factor: 5.157

10.  A mutant of Escherichia coli conditionally defective in the synthesis of holo-[acyl carrier protein].

Authors:  M L Polacco; J E Cronan
Journal:  J Biol Chem       Date:  1981-06-10       Impact factor: 5.157

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  12 in total

1.  Stereochemical modification of geminal dialkyl substituents on pantothenamides alters antimicrobial activity.

Authors:  Annabelle Hoegl; Hamed Darabi; Elisa Tran; Emelia Awuah; Eleanor S C Kerdo; Eric Habib; Kevin J Saliba; Karine Auclair
Journal:  Bioorg Med Chem Lett       Date:  2014-06-18       Impact factor: 2.823

2.  Geminal dialkyl derivatives of N-substituted pantothenamides: synthesis and antibacterial activity.

Authors:  T Olukayode Akinnusi; Kenward Vong; Karine Auclair
Journal:  Bioorg Med Chem       Date:  2011-03-04       Impact factor: 3.641

3.  Structural insights into phosphopantetheinyl hydrolase PptH from Mycobacterium tuberculosis.

Authors:  John Mosior; Ronnie Bourland; Shivatheja Soma; Carl Nathan; James Sacchettini
Journal:  Protein Sci       Date:  2020-01-20       Impact factor: 6.725

4.  Pantethine rescues phosphopantothenoylcysteine synthetase and phosphopantothenoylcysteine decarboxylase deficiency in Escherichia coli but not in Pseudomonas aeruginosa.

Authors:  Carl J Balibar; Micah F Hollis-Symynkywicz; Jianshi Tao
Journal:  J Bacteriol       Date:  2011-05-06       Impact factor: 3.490

5.  The antibiotic CJ-15,801 is an antimetabolite that hijacks and then inhibits CoA biosynthesis.

Authors:  Renier van der Westhuyzen; Justin C Hammons; Jordan L Meier; Samira Dahesh; Wessel J A Moolman; Stephen C Pelly; Victor Nizet; Michael D Burkart; Erick Strauss
Journal:  Chem Biol       Date:  2012-05-25

6.  Exploring structural motifs necessary for substrate binding in the active site of Escherichia coli pantothenate kinase.

Authors:  Emelia Awuah; Eric Ma; Annabelle Hoegl; Kenward Vong; Eric Habib; Karine Auclair
Journal:  Bioorg Med Chem       Date:  2014-04-24       Impact factor: 3.641

7.  Adipostatins E-J, New Potent Antimicrobials Identified as Inhibitors of Coenzyme-A Biosynthesis.

Authors:  Lyanne Gómez-Rodríguez; Pamela J Schultz; Giselle Tamayo-Castillo; Garry D Dotson; David H Sherman; Ashootosh Tripathi
Journal:  Tetrahedron Lett       Date:  2019-12-02       Impact factor: 2.415

8.  Combination of pantothenamides with vanin inhibitors as a novel antibiotic strategy against gram-positive bacteria.

Authors:  Patrick A M Jansen; Pedro H H Hermkens; Patrick L J M Zeeuwen; Peter N M Botman; Richard H Blaauw; Peter Burghout; Peter M van Galen; Johan W Mouton; Floris P J T Rutjes; Joost Schalkwijk
Journal:  Antimicrob Agents Chemother       Date:  2013-07-22       Impact factor: 5.191

9.  Pantothenamides are potent, on-target inhibitors of Plasmodium falciparum growth when serum pantetheinase is inactivated.

Authors:  Christina Spry; Cristiano Macuamule; Zhiyang Lin; Kristopher G Virga; Richard E Lee; Erick Strauss; Kevin J Saliba
Journal:  PLoS One       Date:  2013-02-06       Impact factor: 3.240

10.  A cross-metathesis approach to novel pantothenamide derivatives.

Authors:  Jinming Guan; Matthew Hachey; Lekha Puri; Vanessa Howieson; Kevin J Saliba; Karine Auclair
Journal:  Beilstein J Org Chem       Date:  2016-05-13       Impact factor: 2.883

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