Literature DB >> 5435685

Products of aminolysis and enzymic hydrolysis of the cephalosporins.

J M Hamilton-Miller, G G Newton, E P Abraham.   

Abstract

1. The reaction of cephalosporins with ammonia, amino acids and other simple amino compounds in weakly alkaline aqueous solutions yields labile compounds with lambda(max.) 230nm. The reaction of deacetyl- and deacetoxy-cephalosporins under similar conditions yields compounds with lambda(max.) 260nm. 2. Hydrolysis with a beta-lactamase results in the formation of compounds with lambda(max.) 230nm from deacetylcephalosporins and cephalosporins, but not from deacetoxycephalosporins. 3. These different compounds decompose to give penaldates and penamaldates derived from the side chain and the carbon atoms of the beta-lactam ring. 4. Derivatives similar to those obtained with simple amino compounds appear to be formed when cephalosporins and their analogues react with lysine polymers. 5. Some of the chemical and physical properties of the various derivatives have been studied and tentative structures for them are proposed. 6. Possible implications of the results in relation to the immunological properties of the cephalosporins are discussed.

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Year:  1970        PMID: 5435685      PMCID: PMC1185375          DOI: 10.1042/bj1160371

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


  20 in total

1.  Incorporation of acetate into cephalosporin C.

Authors:  P W TROWN; E P ABRAHAM; G G NEWTON; C W HALE; G A MILLER
Journal:  Biochem J       Date:  1962-07       Impact factor: 3.857

2.  Deacetylcephalosporin C.

Authors:  J D JEFFERY; E P ABRAHAM; G G NEWTON
Journal:  Biochem J       Date:  1961-12       Impact factor: 3.857

3.  Peptide separation by two-dimensional chromatography and electrophoresis.

Authors:  A M KATZ; W J DREYER; C B ANFINSEN
Journal:  J Biol Chem       Date:  1959-11       Impact factor: 5.157

4.  The action of trypsin on polylysine.

Authors:  S G WALEY; J WATSON
Journal:  Biochem J       Date:  1953-09       Impact factor: 3.857

5.  Interaction of cephaloridine with penicillinase-producing gram-negative bacteria.

Authors:  J M Hamilton-Miller; J T Smith; R Knox
Journal:  Nature       Date:  1965-10-16       Impact factor: 49.962

6.  Catalysis by poly-L-lysine of aminolysis of penicillin by tris(hydroxymethyl)aminomethane.

Authors:  M A Schwartz
Journal:  J Med Chem       Date:  1969-01       Impact factor: 7.446

7.  Penicillin allergy: the formation of the penicilloyl determinant.

Authors:  F R Batchelor; J M Dewdney; D Gazzard
Journal:  Nature       Date:  1965-04-24       Impact factor: 49.962

8.  Preliminary observations on the formation and breakdown of "cephalosporoic acids".

Authors:  G G Newton; E P Abraham; S Kuwabara
Journal:  Antimicrob Agents Chemother (Bethesda)       Date:  1967

9.  Cephalosporinase and penicillinase activities of a beta-lactamase from Pseudomonas pyocyanea.

Authors:  L D Sabath; M Jago; E P Abraham
Journal:  Biochem J       Date:  1965-09       Impact factor: 3.857

10.  Changes in proton-magnetic-resonance spectra during aminolysis and enzymic hydrolysis of cephalosporins.

Authors:  J M Hamilton-Miller; E Richards; E P Abraham
Journal:  Biochem J       Date:  1970-02       Impact factor: 3.857

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  16 in total

1.  In vitro activity of Ro 24-6392, a novel ester-linked co-drug combining ciprofloxacin and desacetylcefotaxime.

Authors:  R N Jones
Journal:  Eur J Clin Microbiol Infect Dis       Date:  1990-06       Impact factor: 3.267

2.  A new cephalosporin with a dual mode of action.

Authors:  C H O'Callaghan; R B Sykes; S E Staniforth
Journal:  Antimicrob Agents Chemother       Date:  1976-08       Impact factor: 5.191

3.  Dual-Pharmacophore Pyrithione-Containing Cephalosporins Kill Both Replicating and Nonreplicating Mycobacterium tuberculosis.

Authors:  Landys Lopez Quezada; Kelin Li; Stacey L McDonald; Quyen Nguyen; Andrew J Perkowski; Cameron W Pharr; Ben Gold; Julia Roberts; Kathrine McAulay; Kohta Saito; Selin Somersan Karakaya; Prisca Elis Javidnia; Esther Porras de Francisco; Manuel Marin Amieva; Sara Palomo Dı Az; Alfonso Mendoza Losana; Matthew Zimmerman; Hsin-Pin Ho Liang; Jun Zhang; Veronique Dartois; Stéphanie Sans; Sophie Lagrange; Laurent Goullieux; Christine Roubert; Carl Nathan; Jeffrey Aubé
Journal:  ACS Infect Dis       Date:  2019-06-11       Impact factor: 5.084

4.  Inactivation of Mycobacterium tuberculosis l,d-transpeptidase LdtMt₁ by carbapenems and cephalosporins.

Authors:  Vincent Dubée; Sébastien Triboulet; Jean-Luc Mainardi; Mélanie Ethève-Quelquejeu; Laurent Gutmann; Arul Marie; Lionel Dubost; Jean-Emmanuel Hugonnet; Michel Arthur
Journal:  Antimicrob Agents Chemother       Date:  2012-05-21       Impact factor: 5.191

5.  Syntheses and biological evaluation of new cephalosporin-oxazolidinone conjugates.

Authors:  Shanshan Yan; Marvin J Miller; Timothy A Wencewicz; Ute Möollmann
Journal:  Medchemcomm       Date:  2010-05-05       Impact factor: 3.597

6.  Correlation between hydrolysis of the -lactam bond of the cephalosporin nucleus and expulsion of the 3-substituent.

Authors:  C H O'Callaghan; S M Kirby; A Morris; R E Waller; R E Duncombe
Journal:  J Bacteriol       Date:  1972-06       Impact factor: 3.490

7.  Mouse anti-benzylpenicilloyl IgE monoclonal antibody: preparation, characterization and cross-reactivity.

Authors:  H Fukushima; R Misaki; M Takeuchi; Y Niinomi; M Harada
Journal:  Clin Exp Immunol       Date:  1987-05       Impact factor: 4.330

8.  Changes in proton-magnetic-resonance spectra during aminolysis and enzymic hydrolysis of cephalosporins.

Authors:  J M Hamilton-Miller; E Richards; E P Abraham
Journal:  Biochem J       Date:  1970-02       Impact factor: 3.857

9.  The acyl-enzyme mechanism of beta-lactamase action. The evidence for class C Beta-lactamases.

Authors:  V Knott-Hunziker; S Petursson; S G Waley; B Jaurin; T Grundström
Journal:  Biochem J       Date:  1982-11-01       Impact factor: 3.857

10.  Kinetics and mechanism of zinc ion-mediated degradation of cephalosporins in tromethamine solution.

Authors:  H Tomida; K Kohashi; Y Tsuruta; S Kiryu; M A Schwartz
Journal:  Pharm Res       Date:  1987-06       Impact factor: 4.200

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