Synthesis, Purification and Kinetic Properties of Fluorescein-labelled Penicillins

Overview

Journal Biochem J

Specialty Biochemistry

Date 1994 May 15

PMID 8198525

Citations 25

Authors

B Lakaye

C Damblon

M Jamin

M Galleni

S Lepage

B Joris

J Marchand-Brynaert

C Frydrych

J M Frere

Affiliations

Soon will be listed here.

Abstract

The synthesis and properties of six fluorescein-labelled penicillins are reported. The two isomers of fluoresceyl-glycyl-6-amino-penicillanic acid are probably the best compounds to use for detection of all the penicillin-binding proteins (PBPs) present in a bacterial membrane preparation. However, the derivatives of ampicillin were much more efficient against Enterobacter aerogenes PBP3. The two isomers obtained when a commercial mixture of the two isomers of carboxyfluorescein was used most often exhibited similar properties, but the Streptomyces R61 extracellular DD-peptidase was only efficiently acylated by the 5'-carboxyfluorescein derivative of glycyl-6-aminopenicillanic acid.

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References

Varetto L, Frere J, Nguyen-Disteche M, Ghuysen J, Houssier C . The pH dependence of the active-site serine DD-peptidase of Streptomyces R61. Eur J Biochem. 1987; 162(3):525-31. DOI: 10.1111/j.1432-1033.1987.tb10671.x. View

Jamin M, Hakenbeck R, Frere J . Penicillin binding protein 2x as a major contributor to intrinsic beta-lactam resistance of Streptococcus pneumoniae. FEBS Lett. 1993; 331(1-2):101-4. DOI: 10.1016/0014-5793(93)80305-e. View

Nieto M, Perkins H, Frere J, Ghuysen J . Fluorescence and circular dichroism studies on the Streptomyces R61 DD-carboxypeptidase-transpeptidase. Penicillin binding by the enzyme. Biochem J. 1973; 135(3):493-505. PMC: 1165851. DOI: 10.1042/bj1350493. View

Frere J, LEYH-BOUILLE M, Ghuysen J, Perkins H . Interaction between beta-lactam antibiotics and exocellular DD-carboxypeptidase-transpeptidase of Streptomyces R61. Eur J Biochem. 1974; 50(1):203-14. DOI: 10.1111/j.1432-1033.1974.tb03889.x. View

Spratt B, Pardee A . Penicillin-binding proteins and cell shape in E. coli. Nature. 1975; 254(5500):516-7. DOI: 10.1038/254516a0. View

Frere J, Moreno R, Ghuysen J . Molecular weight, amino acid composition and physicochemical properties of the exocellular DD-carboxypeptidase-transpeptidase of Streptomyces R39. Biochem J. 1974; 143(1):233-40. PMC: 1168371. DOI: 10.1042/bj1430233. View

Frere J, Ghuysen J, IWATSUBO M . Kinetics of interaction between the exocellular DD-carboxypeptidase-transpeptidase from Streptomyces R61 and beta-lactam antibiotics. A choice of models. Eur J Biochem. 1975; 57(2):343-51. DOI: 10.1111/j.1432-1033.1975.tb02307.x. View

Spratt B . Properties of the penicillin-binding proteins of Escherichia coli K12,. Eur J Biochem. 1977; 72(2):341-52. DOI: 10.1111/j.1432-1033.1977.tb11258.x. View

Curtis N, Orr D, Ross G, Boulton M . Affinities of penicillins and cephalosporins for the penicillin-binding proteins of Escherichia coli K-12 and their antibacterial activity. Antimicrob Agents Chemother. 1979; 16(5):533-9. PMC: 352901. DOI: 10.1128/AAC.16.5.533. View

10.

Kelly J, Frere J, Klein D, Ghuysen J . Interaction between non-classical beta-lactam compounds and the Zn2+-containing G and serine R61 and R39 D-alanyl-D-alanine peptidases. Biochem J. 1981; 199(1):129-36. PMC: 1163342. DOI: 10.1042/bj1990129. View

11.

Frere J, Joris B . Penicillin-sensitive enzymes in peptidoglycan biosynthesis. Crit Rev Microbiol. 1985; 11(4):299-396. DOI: 10.3109/10408418409105906. View

12.

Curtis N, Eisenstadt R, Rudd C, White A . Inducible type I beta-lactamases of gram-negative bacteria and resistance to beta-lactam antibiotics. J Antimicrob Chemother. 1986; 17(1):51-61. DOI: 10.1093/jac/17.1.51. View

13.

De Meester F, Joris B, Reckinger G, Frere J, WALEY S . Automated analysis of enzyme inactivation phenomena. Application to beta-lactamases and DD-peptidases. Biochem Pharmacol. 1987; 36(14):2393-403. DOI: 10.1016/0006-2952(87)90609-5. View

14.

Bellido F, Veuthey C, Blaser J, Bauernfeind A, Pechere J . Novel resistance to imipenem associated with an altered PBP-4 in a Pseudomonas aeruginosa clinical isolate. J Antimicrob Chemother. 1990; 25(1):57-68. DOI: 10.1093/jac/25.1.57. View

15.

Piras G, El Kharroubi A, Van Beeumen J, Coeme E, Coyette J, Ghuysen J . Characterization of an Enterococcus hirae penicillin-binding protein 3 with low penicillin affinity. J Bacteriol. 1990; 172(12):6856-62. PMC: 210803. DOI: 10.1128/jb.172.12.6856-6862.1990. View

16.

Laible G, Spratt B, Hakenbeck R . Interspecies recombinational events during the evolution of altered PBP 2x genes in penicillin-resistant clinical isolates of Streptococcus pneumoniae. Mol Microbiol. 1991; 5(8):1993-2002. DOI: 10.1111/j.1365-2958.1991.tb00821.x. View

17.

Hadonou A, Jamin M, Adam M, Joris B, Dusart J, Ghuysen J . Importance of the His-298 residue in the catalytic mechanism of the Streptomyces R61 extracellular DD-peptidase. Biochem J. 1992; 282 ( Pt 2):495-500. PMC: 1130807. DOI: 10.1042/bj2820495. View

18.

Galleni M, Lakaye B, Lepage S, Jamin M, Thamm I, Joris B . A new, highly sensitive method for the detection and quantification of penicillin-binding proteins. Biochem J. 1993; 291 ( Pt 1):19-21. PMC: 1132474. DOI: 10.1042/bj2910019. View

19.

Jamin M, Damblon C, Millier S, Hakenbeck R, Frere J . Penicillin-binding protein 2x of Streptococcus pneumoniae: enzymic activities and interactions with beta-lactams. Biochem J. 1993; 292 ( Pt 3):735-41. PMC: 1134175. DOI: 10.1042/bj2920735. View

20.

Linstrom E, Boman H, STEELE B . Resistance of Escherichia coli to penicillins. VI. Purification and characterization of the chromosomally mediated penicillinase present in ampA-containing strains. J Bacteriol. 1970; 101(1):218-31. PMC: 250473. DOI: 10.1128/jb.101.1.218-231.1970. View