Synthesis of Penicillin: 6-Aminopenicillanic Acid in Penicillin Fermentations

@article{Batchelor1959SynthesisOP,
  title={Synthesis of Penicillin: 6-Aminopenicillanic Acid in Penicillin Fermentations},
  author={F. R. Batchelor and Frank Peter Doyle and John Herbert Charles Nayler and George Newbolt Rolinson},
  journal={Nature},
  year={1959},
  volume={183},
  pages={257-258}
}
THE work reported here stemmed from the experiments described in an earlier communication1 on p-aminobenzylpenicillin, in which discrepancies were observed between chemical and biological methods of penicillin assay when a precursor was omitted from penicillin fermentations. 
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334 Citations
Highly Influential Citations
3
Background Citations
22
Methods Citations
2
Results Citations
1

334 Citations

A Method for isolating Bacteria capable of producing 6-Aminopenicillanic Acid from Benzylpenicillin
TLDR
The isolation of 6-aminopenicillanic acid (I) from a submerged culture of Penicillium chrysogenum and its preparation by the microbial hydrolysis of benzylpenicillin (II) was discussed.
Production of 6-Aminopenicillanic Acid by Dermatophytes
TLDR
This work has reported on production of 6-APA by certain species of Cephalosporium and Emericellopsis and on its formation both by fermentation and by microbial hydrolysis.
Comparative Studies of Penicillinase Induction in Microorganisms by Natural and Semi- Synthetic Penicillins
Author Institution: Department of Chemistry and Department of Biological Chemistry of the College of Medicine, University of Cincinnati, Cincinnati 21
Chemistry and Biosynthesis of Penicillins and Cephalosporins
It has now been more than 50 years since Fleming’s legendary observations on the inhibition of bacterial growth by Penicillium notatum laid the foundations of modern antibiotic chemotherapy.
Clinical pharmacology of the semisynthetic penicillins
  • P. Dineen
  • Medicine
    Clinical pharmacology and therapeutics
  • 1962
TLDR
The semisynthetic penicillin compounds are the product of the addition of various prosthetic groups to a basic building block, 6‐aminopenicillanic acid.
Biological assay of cephalosporin C.
SUMMARY: A method of assaying the antibiotic cephalosporin C in low concentration in culture fluids by using a strain of Vibrio cholerae is described. The formation of spheroplasts of the test…
6 -amidinopenicillanic acids--a new group of antibiotics.
TLDR
Findings are reported on a new type of N-substituted 6-aminopenicillanic acids with improved oral absorption, resistance to penicillinase and increased activity towards Gram-negative bacilli.
Antibacterial activity of penicillin I. The nature of the activity of different acyl derivatives of 6-aminopenicillanic acid
  • G. Rolinson
  • Biology
    Proceedings of the Royal Society of London. Series B. Biological Sciences
  • 1965
TLDR
The results obtained are consistent with the view that differences in activity between one penicillin and another are due to differences in affinity between the antibiotic and the bacterial cell, rather than to Differences in the function of the drug once the antibiotic has reached the site of action.
A quantitative microbiological determination of 6-aminopenicillanic acid
TLDR
A specific microbiological plate assay withSerratia marcescens D 217 (ATCC 27117) is described for estimating even small amounts of 6-APA in benzyl- and phenoxymethylpenicillin samples.
Biosynthesis of Cephalosporin C: I. Factors Affecting the Fermentation.
TLDR
No evidence was found for precursor action such as is found in penicillin fermentations, but the ability of resting cells to produce antibiotic was demonstrated and l-Cystine had a greater enhancing effect on formation of cephalosporin C than on formation in synthetic media.
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References

SHOWING 1-3 OF 3 REFERENCES
Penicillin Derivatives of p-Aminobenzyl-penicillin
TLDR
The work reported here was carried out in order to obtain p-aminobenzylpenicillin for use as the parent compound of a series of derivatives.
THE SYNTHESIS OF SUBSTITUTED PENICILLINS AND SIMPLER STRUCTURAL ANALOGS. VII. THE CYCLIZATION OF A PENICILLOATE DERIVATIVE TO METHYL PHTHALIMIDOPENICILLANATE
The chemistry of penicillin