Literature DB >> 31362987

Recognition of the β-lactam carboxylate triggers acylation of Neisseria gonorrhoeae penicillin-binding protein 2.

Avinash Singh1, Joshua Tomberg2, Robert A Nicholas2,3, Christopher Davies4.   

Abstract

Resistance of Neisseria gonorrhoeae to extended-spectrum cephalosporins (ESCs) has become a major threat to human health. The primary mechanism by which N. gonorrhoeae becomes resistant to ESCs is by acquiring a mosaic penA allele, encoding penicillin-binding protein 2 (PBP2) variants containing up to 62 mutations compared with WT, of which a subset contribute to resistance. To interpret molecular mechanisms underpinning cephalosporin resistance, it is necessary to know how PBP2 is acylated by ESCs. Here, we report the crystal structures of the transpeptidase domain of WT PBP2 in complex with cefixime and ceftriaxone, along with structures of PBP2 in the apo form and with a phosphate ion bound in the active site at resolutions of 1-7-1.9 Å. These structures reveal that acylation of PBP2 by ESCs is accompanied by rotation of the Thr-498 side chain in the KTG motif to contact the cephalosporin carboxylate, twisting of the β3 strand to form the oxyanion hole, and rolling of the β3-β4 loop toward the active site. Recognition of the cephalosporin carboxylate appears to be the key trigger for formation of an acylation-competent state of PBP2. The structures also begin to explain the impact of mutations implicated in ESC resistance. In particular, a G545S mutation may hinder twisting of β3 because its side chain hydroxyl forms a hydrogen bond with Thr-498. Overall, our data suggest that acylation is initiated by conformational changes elicited or trapped by binding of ESCs and that these movements are restricted by mutations associated with resistance against ESCs.
© 2019 Singh et al.

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Keywords:  Neisseria gonorrhoeae; acylation mechanism; antibiotic action; bacteria; cephalosporin resistance; conformational chages; crystal structure; penicillin-binding protein; peptidoglycan; protein structure

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Year:  2019        PMID: 31362987      PMCID: PMC6755799          DOI: 10.1074/jbc.RA119.009942

Source DB:  PubMed          Journal:  J Biol Chem        ISSN: 0021-9258            Impact factor:   5.157


  53 in total

1.  BOCILLIN FL, a sensitive and commercially available reagent for detection of penicillin-binding proteins.

Authors:  G Zhao; T I Meier; S D Kahl; K R Gee; L C Blaszczak
Journal:  Antimicrob Agents Chemother       Date:  1999-05       Impact factor: 5.191

2.  Refinement of macromolecular structures by the maximum-likelihood method.

Authors:  G N Murshudov; A A Vagin; E J Dodson
Journal:  Acta Crystallogr D Biol Crystallogr       Date:  1997-05-01

3.  Structural basis for the beta lactam resistance of PBP2a from methicillin-resistant Staphylococcus aureus.

Authors:  Daniel Lim; Natalie C J Strynadka
Journal:  Nat Struct Biol       Date:  2002-11

4.  Crystal structure of Escherichia coli penicillin-binding protein 5 bound to a tripeptide boronic acid inhibitor: a role for Ser-110 in deacylation.

Authors:  George Nicola; Sridhar Peddi; Miglena Stefanova; Robert A Nicholas; William G Gutheil; Christopher Davies
Journal:  Biochemistry       Date:  2005-06-14       Impact factor: 3.162

5.  Mutations in ponA, the gene encoding penicillin-binding protein 1, and a novel locus, penC, are required for high-level chromosomally mediated penicillin resistance in Neisseria gonorrhoeae.

Authors:  Patricia A Ropp; Mei Hu; Melanie Olesky; Robert A Nicholas
Journal:  Antimicrob Agents Chemother       Date:  2002-03       Impact factor: 5.191

6.  The crystal structure of the penicillin-binding protein 2x from Streptococcus pneumoniae and its acyl-enzyme form: implication in drug resistance.

Authors:  E Gordon; N Mouz; E Duée; O Dideberg
Journal:  J Mol Biol       Date:  2000-06-02       Impact factor: 5.469

7.  A PBP2x from a clinical isolate of Streptococcus pneumoniae exhibits an alternative mechanism for reduction of susceptibility to beta-lactam antibiotics.

Authors:  Lucile Pernot; Laurent Chesnel; Audrey Le Gouellec; Jacques Croizé; Thierry Vernet; Otto Dideberg; Andréa Dessen
Journal:  J Biol Chem       Date:  2004-01-20       Impact factor: 5.157

8.  The perfect penicillin? Inhibition of a bacterial DD-peptidase by peptidoglycan-mimetic beta-lactams.

Authors:  Helen R Josephine; Ish Kumar; R F Pratt
Journal:  J Am Chem Soc       Date:  2004-07-07       Impact factor: 15.419

9.  The crystal structure of phosphonate-inhibited D-Ala-D-Ala peptidase reveals an analogue of a tetrahedral transition state.

Authors:  Nicholas R Silvaggi; John W Anderson; Shaun R Brinsmade; R F Pratt; Judith A Kelly
Journal:  Biochemistry       Date:  2003-02-11       Impact factor: 3.162

10.  Identification and analysis of amino acid mutations in porin IB that mediate intermediate-level resistance to penicillin and tetracycline in Neisseria gonorrhoeae.

Authors:  Melanie Olesky; Marcia Hobbs; Robert A Nicholas
Journal:  Antimicrob Agents Chemother       Date:  2002-09       Impact factor: 5.191

View more
  5 in total

1.  Mutations in penicillin-binding protein 2 from cephalosporin-resistant Neisseria gonorrhoeae hinder ceftriaxone acylation by restricting protein dynamics.

Authors:  Avinash Singh; Jonathan M Turner; Joshua Tomberg; Alena Fedarovich; Magnus Unemo; Robert A Nicholas; Christopher Davies
Journal:  J Biol Chem       Date:  2020-04-06       Impact factor: 5.157

Review 2.  β-Lactam antibiotic targets and resistance mechanisms: from covalent inhibitors to substrates.

Authors:  Montserrat Mora-Ochomogo; Christopher T Lohans
Journal:  RSC Med Chem       Date:  2021-08-04

3.  Impact of the gonococcal FC428 penA allele 60.001 on ceftriaxone resistance and biological fitness.

Authors:  Ke Zhou; Shao-Chun Chen; Fan Yang; Stijn van der Veen; Yue-Ping Yin
Journal:  Emerg Microbes Infect       Date:  2020-12       Impact factor: 7.163

4.  Dissemination and genome analysis of high-level ceftriaxone-resistant penA 60.001 Neisseria gonorrhoeae strains from the Guangdong Gonococcal antibiotics susceptibility Programme (GD-GASP), 2016-2019.

Authors:  Xiaomian Lin; Wentao Chen; Qinghui Xie; Yuqi Yu; Yiwen Liao; Zhanjin Feng; Xiaolin Qin; Xingzhong Wu; Sanmei Tang; Heping Zheng
Journal:  Emerg Microbes Infect       Date:  2022-12       Impact factor: 7.163

Review 5.  Establishing Novel Molecular Algorithms to Predict Decreased Susceptibility to Ceftriaxone in Neisseria gonorrhoeae Strains.

Authors:  Eric Y Lin; Paul C Adamson; Xiaomeng Deng; Jeffrey D Klausner
Journal:  J Infect Dis       Date:  2021-04-08       Impact factor: 5.226

  5 in total

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