Literature DB >> 175787

Synthesis of tritium-labelled isopenicillin N, penicillin N and 6-aminopenicillanic acid.

J J Usher, B Loder, E P Abraham.   

Abstract

1. Phenoxymethylpenicillin sulphoxide 4-methoxybenzyl ester was labelled with 3H in its 2-beta-methyl group. Its specific radioactivity was 362 mCi/mmol. 2. Removal of the side chain of this compound yielded the corresponding ester of 6-aminopenicillanic acid sulphoxide and coupling of the latter with the appropriate protected alpha-aminoadipic acid gave 4-methoxybenzyloxycarbonylisopenicillin N sulphoxide di-4-methoxybenzyl ester or the corresponding derivative of penicillin N. 3. Removal of the protective groups by hydrogenolysis and reduction of the sulphoxide group yielded 3H-labelled isopenicillin N or penicillin N. 4. 3H-labelled phenoxymethylpenicillin sulphoxide was obtained by hydrogenolysis from its 4-methoxybenzyl ester. Reduction of its sulphoxide group and subsequent removal of the side chain gave 3H-labelled 6-aminopenicillanic acid.

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Year:  1975        PMID： 175787      PMCID： PMC1172422          DOI： 10.1042/bj1510729

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


  18 in total

1.  Aminoadipylpenicillin in penicillin fermentations.

Authors:  M COLE; F R BATCHELOR
Journal:  Nature       Date:  1963       Impact factor: 49.962

2.  The structure of cephalesporin C.

Authors:  E P ABRAHAM; G G NEWTON
Journal:  Biochem J       Date:  1961-05       Impact factor: 3.857

3.  Derivatives of cephalosporin C formed with certain heterocyclic tertiary bases. The cephalosporin C-A family.

Authors:  C W HALE; G G NEWTON; E P ABRAHAM
Journal:  Biochem J       Date:  1961-05       Impact factor: 3.857

4.  Colorimetric detection of penicillins and cephalosporins on paper.

Authors:  R THOMAS
Journal:  Nature       Date:  1961-09-16       Impact factor: 49.962

5.  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

6.  [Amino acid determination on paper chromatograms].

Authors:  J HEILMANN; J BARROLLIER; E WATZKE
Journal:  Hoppe Seylers Z Physiol Chem       Date:  1957

7.  Synthesis of D-delta-amino-delta-carboxyvalerylglycine (a degradation product of cephalosporin N) and of DL-delta-amino-delta-carboxyvaleramide.

Authors:  E P ABRAHAM; G G NEWTON
Journal:  Biochem J       Date:  1954-10       Impact factor: 3.857

8.  Energetics of peptide formation.

Authors:  J W BREITENBACH; J DERKOSCH; F WESSELY
Journal:  Nature       Date:  1952-05-31       Impact factor: 49.962

9.  Chemistry of cephalosporin antibiotics. 23. 2-Methyl- and 2-methylenecephalosporins.

Authors:  I G Wright; C W Ashbrook; T Goodson; G V Kaiser; E M Van Heyningen
Journal:  J Med Chem       Date:  1971-05       Impact factor: 7.446

10.  Preparation of penicillin N and isopenicillin N.

Authors:  H Vanderhaeghe; A Vlietinck; M Claesen; G Parmentier
Journal:  J Antibiot (Tokyo)       Date:  1974-03       Impact factor: 2.649
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  11 in total

1.  6 beta-Bromopenicillanic acid inactivates beta-lactamase I.

Authors:  V Knott-Hunziker; B S Orlek; P G Sammes; S G Waley
Journal:  Biochem J       Date:  1979-01-01       Impact factor: 3.857

2.  Structural studies on the reaction of isopenicillin N synthase with the substrate analogue delta-(l-alpha-aminoadipoyl)-l-cysteinyl-d-alpha-aminobutyrate.

Authors:  Alexandra J Long; Ian J Clifton; Peter L Roach; Jack E Baldwin; Christopher J Schofield; Peter J Rutledge
Journal:  Biochem J       Date:  2003-06-15       Impact factor: 3.857

3.  Investigations into the post-translational modification and mechanism of isopenicillin N:acyl-CoA acyltransferase using electrospray mass spectrometry.

Authors:  R T Aplin; J E Baldwin; P L Roach; C V Robinson; C J Schofield
Journal:  Biochem J       Date:  1993-09-01       Impact factor: 3.857

4.  Active sites of beta-lactamases. The chromosomal beta-lactamases of Pseudomonas aeruginosa and Escherichia coli.

Authors:  V Knott-Hunziker; S Petursson; G S Jayatilake; S G Waley; B Jaurin; T Grundström
Journal:  Biochem J       Date:  1982-03-01       Impact factor: 3.857

5.  Behaviour of tritium-labelled isopenicillin N and 6-aminopenicillanic acid as potential penicillin precursors in an extract of Penicillum chrysogenum.

Authors:  P A Fawcett; J J Usher; E P Abraham
Journal:  Biochem J       Date:  1975-12       Impact factor: 3.857

6.  Cell-free conversion of delta-(L-alpha-aminoadipyl)-L-cysteinyl-D-valine into an antibiotic with the properties of isopenicillin N in Cephalosporium acremonium.

Authors:  T Konomi; S Herchen; J E Baldwin; M Yoshida; N A Hunt; A L Demain
Journal:  Biochem J       Date:  1979-11-15       Impact factor: 3.857

7.  Synthesis of delta-(alpha-aminoadipyl)cysteinylvaline and its role in penicillin biosynthesis.

Authors:  P A Fawcett; J J Usher; J A Huddleston; R C Bleaney; J J Nisbet; E P Abraham
Journal:  Biochem J       Date:  1976-09-01       Impact factor: 3.857

8.  Incorporation of 3H and 14C from (6 alpha-3H)penicillin N and (10-14C,6 alpha-3H) penicillin N into deacetoxycephalosporin C.

Authors:  J E Baldwin; P D Singh; M Yoshida; Y Sawada; A L Demain
Journal:  Biochem J       Date:  1980-03-15       Impact factor: 3.857

9.  Conversion of isopenicillin N into penicillin N in cell-free extracts of Cephalosporium acremonium.

Authors:  G S Jayatilake; J A Huddleston; E P Abraham
Journal:  Biochem J       Date:  1981-02-15       Impact factor: 3.857

10.  Incorporation of 3H from delta-(L-alpha-amino (4,5-3H)adipyl)-L-cysteinyl-D-(4,4-3H)valine into isopenicillin N.

Authors:  J O'Sullivan; R C Bleaney; J A Huddleston; E P Abraham
Journal:  Biochem J       Date:  1979-11-15       Impact factor: 3.857
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