Literature DB >> 3066349

Evidence for an oxyanion hole in serine beta-lactamases and DD-peptidases.

B P Murphy1, R F Pratt.   

Abstract

A thionocephalosporin is shown to be a much poorer substrate of representative serine beta-lactamases of class A (RTEM-2) and class C (Enterobacter cloacae P99) and a much poorer inhibitor of the Streptomyces R61 DD-peptidase than is the analogous oxo beta-lactam. These results provide kinetic evidence for the existence of a catalytic oxyanion hole in these enzymes.

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Year:  1988        PMID： 3066349      PMCID： PMC1135462          DOI： 10.1042/bj2560669

Source DB:  PubMed          Journal:  Biochem J        ISSN： 0264-6021            Impact factor:   3.857


  23 in total

1.  Letter: Beta-thionolactam analogs of cephalosporins and penicillins.

Authors:  P W Wojtkowski; J E Dolfini; O Kocy; C M Cimarusti
Journal:  J Am Chem Soc       Date:  1975-09-17       Impact factor: 15.419

2.  Statistical estimations in enzyme kinetics.

Authors:  G N WILKINSON
Journal:  Biochem J       Date:  1961-08       Impact factor: 3.857

3.  Penicillinase active sites: labelling of serine-44 in beta-lactamase I by 6beta-bromopenicillanic acid.

Authors:  V Knott-Hunziker; S G Waley; B S Orlek; P G Sammes
Journal:  FEBS Lett       Date:  1979-03-01       Impact factor: 4.124

Review 4.  Serine proteases: structure and mechanism of catalysis.

Authors:  J Kraut
Journal:  Annu Rev Biochem       Date:  1977       Impact factor: 23.643

5.  Subtilisin; a stereochemical mechanism involving transition-state stabilization.

Authors:  J D Robertus; J Kraut; R A Alden; J J Birktoft
Journal:  Biochemistry       Date:  1972-11-07       Impact factor: 3.162

6.  Chymotrypsin-catalyzed phenyl ester hydrolysis. Evidence for electrophilic assistance on carbonyl oxygen.

Authors:  A Williams
Journal:  Biochemistry       Date:  1970-08-18       Impact factor: 3.162

7.  Mechanism of action of penicillins: a proposal based on their structural similarity to acyl-D-alanyl-D-alanine.

Authors:  D J Tipper; J L Strominger
Journal:  Proc Natl Acad Sci U S A       Date:  1965-10       Impact factor: 11.205

8.  beta-Lactamase proceeds via an acyl-enzyme intermediate. Interaction of the Escherichia coli RTEM enzyme with cefoxitin.

Authors:  J Fisher; J G Belasco; S Khosla; J R Knowles
Journal:  Biochemistry       Date:  1980-06-24       Impact factor: 3.162

9.  Chemistry of cephalosporin antibiotics. XXI. Conversion of penicillins to cephalexin.

Authors:  R R Chauvette; P A Pennington; C W Ryan; R D Cooper; F L José; I G Wright; E M Van Heyningen; G W Huffman
Journal:  J Org Chem       Date:  1971-05-07       Impact factor: 4.354

10.  Fluorescence and circular dichroism studies on the Streptomyces R61 DD-carboxypeptidase-transpeptidase. Penicillin binding by the enzyme.

Authors:  M Nieto; H R Perkins; J M Frère; J M Ghuysen
Journal:  Biochem J       Date:  1973-11       Impact factor: 3.857
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  22 in total

1.  Structural basis for imipenem inhibition of class C beta-lactamases.

Authors:  Beth M Beadle; Brian K Shoichet
Journal:  Antimicrob Agents Chemother       Date:  2002-12       Impact factor: 5.191

Review 2.  Catalytic properties of class A beta-lactamases: efficiency and diversity.

Authors:  A Matagne; J Lamotte-Brasseur; J M Frère
Journal:  Biochem J       Date:  1998-03-01       Impact factor: 3.857

3.  Influence of substrates and inhibitors on the structure of Klebsiella pneumoniae carbapenemase-2.

Authors:  Ben A Shurina; Richard C Page
Journal:  Exp Biol Med (Maywood)       Date:  2019-06-04

4.  In vitro prediction of the evolution of GES-1 β-lactamase hydrolytic activity.

Authors:  Séverine Bontron; Laurent Poirel; Patrice Nordmann
Journal:  Antimicrob Agents Chemother       Date:  2015-01-05       Impact factor: 5.191

Review 5.  The versatility of boron in biological target engagement.

Authors:  Diego B Diaz; Andrei K Yudin
Journal:  Nat Chem       Date:  2017-07-25       Impact factor: 24.427

6.  The crystal structures of CDD-1, the intrinsic class D β-lactamase from the pathogenic Gram-positive bacterium Clostridioides difficile, and its complex with cefotaxime.

Authors:  Nichole K Stewart; Clyde A Smith; Marta Toth; Anastasiya Stasyuk; Sergei B Vakulenko
Journal:  J Struct Biol       Date:  2019-09-21       Impact factor: 2.867

7.  The deacylation mechanism of AmpC beta-lactamase at ultrahigh resolution.

Authors:  Yu Chen; George Minasov; Tomer A Roth; Fabio Prati; Brian K Shoichet
Journal:  J Am Chem Soc       Date:  2006-03-08       Impact factor: 15.419

8.  Substrate selectivity and a novel role in inhibitor discrimination by residue 237 in the KPC-2 beta-lactamase.

Authors:  Krisztina M Papp-Wallace; Magdalena Taracila; John M Hornick; Andrea M Hujer; Kristine M Hujer; Anne M Distler; Andrea Endimiani; Robert A Bonomo
Journal:  Antimicrob Agents Chemother       Date:  2010-04-26       Impact factor: 5.191

9.  Inhibition of the class C beta-lactamase from Acinetobacter spp.: insights into effective inhibitor design.

Authors:  Sarah M Drawz; Maja Babic; Christopher R Bethel; Magda Taracila; Anne M Distler; Claudia Ori; Emilia Caselli; Fabio Prati; Robert A Bonomo
Journal:  Biochemistry       Date:  2010-01-19       Impact factor: 3.162

Review 10.  Three decades of the class A beta-lactamase acyl-enzyme.

Authors:  Jed F Fisher; Shahriar Mobashery
Journal:  Curr Protein Pept Sci       Date:  2009-10       Impact factor: 3.272
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