Home LiteratureArticle Details
PMID: 6299270 Published · ppublish English Journal Article Research Support, Non-U.S. Gov't Research Support, U.S. Gov't, P.H.S.

Interaction of beta-iodopenicillanate with the beta-lactamases of Streptomyces albus G and Actinomadura R39.

The Biochemical journal ·Vol. 207 ·No. 3 ·1982-12-01 ·Pages 437-44

Frère JM, Dormans C, Duyckaerts C, De Graeve J

Abstract

The beta-lactamases of Streptomyces albus G and Actinomadura R39 are inactivated by beta-iodopenicillanate. However, in contrast with the beta-lactamase I from Bacillus cereus, they also efficiently catalyse the hydrolysis of the inactivator; with the S. albus G enzyme, kcat. is larger than 25s-1 and the number of turnovers before inactivation is 515. With the A. R39 enzyme, kcat. is larger than 50s-1 and the number of turnovers before inactivation is 80. After hydrolysis of the beta-lactam amide bond, the product rearranges into 2.3-dihydro-2,2-dimethyl-1,4-thiazine-3,6-dicarboxylate, which exhibits an absorption maximum at 305 nm.

MeSH Terms
Actinomycetaceae/enzymology Hydrolysis Kinetics Mass Spectrometry Models, Biological Penicillanic Acid/metabolism Streptomyces/enzymology beta-Lactamase Inhibitors
Chemicals
beta-Lactamase Inhibitors Penicillanic Acid 6-iodopenicillanic acid
Authors & Affiliations
4 authors, click to expand affiliations / ORCID
Frère J M
Dormans C
Duyckaerts C
De Graeve J
References (20)
20 references, click to expand
  1. Novel method for detection of beta-lactamases by using a chromogenic cephalosporin substrate.
    Antimicrob Agents Chemother. 1972 Apr;1(4):283-8 PMID: 4208895
  2. Kinetics of inactivation of beta-lactamase I by 6 beta-bromopenicillanic acid.
    Biochem J. 1980 Jun 1;187(3):797-802 PMID: 6331385
  3. A semi-synthetic penicillinase inactivator.
    Nature. 1979 Mar 22;278(5702):360-1 PMID: 218114
  4. Penicillinase active sites: labelling of serine-44 in beta-lactamase I by 6beta-bromopenicillanic acid.
    FEBS Lett. 1979 Mar 1;99(1):59-61 PMID: 220094
  5. beta-Lactamase proceeds via an acyl-enzyme intermediate. Interaction of the Escherichia coli RTEM enzyme with cefoxitin.
    Biochemistry. 1980 Jun 24;19(13):2895-901 PMID: 6994800
  6. Inactivation of Bacillus cereus beta-lactamase I by 6 beta-bromopenicillanic acid: kinetics.
    Biochemistry. 1980 Aug 19;19(17):3990-5 PMID: 6250581
  7. Inactivation of Bacillus cereus beta-lactamase I by 6 beta-bromopencillanic acid: mechanism.
    Biochemistry. 1980 Aug 19;19(17):3996-4003 PMID: 6773559
  8. On the chemistry of beta-lactamase inhibition by 6 beta-bromopenicillanic acid.
    J Chem Soc Perkin 1. 1980;10:2322-9 PMID: 6253512
  9. Beta-lactamase inactivation by mechanism-based reagents.
    Philos Trans R Soc Lond B Biol Sci. 1980 May 16;289(1036):309-19 PMID: 6109326
  10. Active site of staphylococcal beta-lactamase.
    Philos Trans R Soc Lond B Biol Sci. 1980 May 16;289(1036):370-2 PMID: 6109335
  11. Inactivation of the RTEM beta-lactamase from Escherichia coli. Interaction of penam sulfones with enzyme.
    Biochemistry. 1981 May 12;20(10):2726-31 PMID: 7018564
  12. Inactivation of RTEM beta-lactamase from Escherichia coli by clavulanic acid and 9-deoxyclavulanic acid.
    Biochemistry. 1981 May 26;20(11):3214-9 PMID: 7018570
  13. 6-beta-bromo- and 6-beta-iodo penicillanic acid, two novel beta-lactamase inhibitors.
    J Antimicrob Chemother. 1981 May;7(5):531-6 PMID: 6267005
  14. 6 beta-Iodopenicillanic acid (UI-38,006), a beta-lactamase inhibitor that extends the antibacterial spectrum of beta-lactam compounds: initial bacteriological characterization.
    Antimicrob Agents Chemother. 1981 Sep;20(3):327-31 PMID: 6272628
  15. The exocellular beta-lactamase of Streptomyces albus G. Purification, properties and comparison with the exocellular DD-carboxypeptidase.
    Biochem J. 1981 Jan 1;193(1):75-82 PMID: 6975618
  16. Purification and properties of the exocellular beta-lactamase of Actinomadura strain R39.
    Biochim Biophys Acta. 1982 Jan 4;700(1):24-32 PMID: 6976797
  17. Isolation of a covalent intermediate in beta -lactamase I catalysis.
    FEBS Lett. 1982 Jan 25;137(2):186-8 PMID: 6800840
  18. Delta 2- and delta 3-cephalosporins, penicillinate and 6-unsubstituted penems. Intrinsic reactivity and interaction with beta-lactamases and D-alanyl-D-alanine-cleaving serine peptidases.
    Biochem J. 1982 Apr 1;203(1):223-34 PMID: 6980645
  19. Interaction of clavulanate with the beta-lactamases of Streptomyces albus G and Actinomadura R39.
    Biochem J. 1982 Dec 1;207(3):429-36 PMID: 6984651
  20. 6-beta-bromopenicillanic acid, a potent beta-lactamase inhibitor.
    Proc Natl Acad Sci U S A. 1978 Sep;75(9):4145-9 PMID: 212736
Article Info
Journal
The Biochemical journal
Abbr.
Biochem J
ISSN
0264-6021
Published
1982-12-01
Pages
437-44
Language
English
Region
England
NLM ID
2984726R
PMCID
PMC1153883
Subset
IM
Grants
NIAID NIH HHS · 2 R01 AI 13364-05 · United States
Analysis Services
Analysis Services

Contact

No. 2 Wenbo Road, Zhangqiu District, Jinan, Shandong

Qilu Normal University · Genelibs Bioinformatics Lab

750 Shunhua Rd, Jinan

2F, Bldg F, University Science Park

Tel: 0531-88819269

WeChat Official Account

Follow our WeChat subscription account for real-time updates and the latest in medical and biological research.


Business Email

E-mail: [email protected]