Microbial Synthesis of Cephalosporin and Penicillin Compounds

Lemke, Paul A.; Brannon, D. R.

doi:10.1016/b978-0-12-261450-7.50014-9

Cited by 23 publications

(10 citation statements)

References 232 publications

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“…Among the fungi, fermentations which yield fi-lactam antibiotics fall into two main types (15): (i) those akin to Penicillium fermentations, and (ii) those related to Cephalosporium fermentations. The Penicillium type of fermentation results in the fornation of a number of penicillins with nonpolar side chains, depending upon available precursors, 6-aminopenicillanic acid, and isQpenicilhin N, which has a 8-linked La-aminoadipyl side chain (11).…”

mentioning

confidence: 99%

“…Although different fermentation patterns are observed among f,-lactam antibiotic-producing microorganisms, a tripeptide intermediate has been implicated as a common precursor for both penicillins and cephalosporins (1,9,15). This tripeptide theory, which has dominated the subject of microbial biosynthesis of fl-lactam antibiotics, was initiated by the isolation of a noncyclic tripeptide (a-aminoadipic acid-cysteinevaline moiety [ACV]) corresponding empirically t Present addres: Analytab Products, Plainview, NY 11803. to penicillin N from the mycelium ofPen icillium chrysogenum (3).…”

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confidence: 99%

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Isolation and nature of intracellular alpha-aminoadipic acid-containing peptides from Paecilomyces persicinus P-10

Eriquez¹,

Pisano²

1979

Antimicrob Agents Chemother

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Small intracellular peptides containing a-aminoadipic acid, cysteine, and a valine moiety were obtained from mycelia of Paecilomyces persicinus P-10 by ethanol or trichloroacetic acid extraction. After performic acid oxidation and ionexchange chromatography, analysis of the peptide fractions by two-dimensional thin-layer electrophoresis and chromatography revealed the presence of three related peptides, as sulfonic acid derivatives, each containing a-aminoadipic acid. Each peptide was isolated in chromatographically pure form by semipreparative thin-layer electrophoresis and chromatography. The purified peptides were subjected to differential hydrolysis, dansylation, and combined dansylation-phenylisothiocyanate sequence analysis. Based on these studies, the structures of the isolated peptides were determined to be (i) glycl-8-(a-aminoadipyl)-cysteinyl-fihydroxyvaline, (ii) glycyl-$-(a-aminoadipyl)-cysteinylvaline, and (iii) 8-(a-aminoadipyl)-cysteinylvaline. The peptides isolated from Paecilomyces are similar to the a-aminoadipic acid-cysteine-valine moiety complex peptides isolated from Cephalosporium.

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confidence: 99%

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confidence: 99%

Isolation and nature of intracellular alpha-aminoadipic acid-containing peptides from Paecilomyces persicinus P-10

Eriquez¹,

Pisano²

1979

Antimicrob Agents Chemother

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“…Extensive reviews exist on the biosynthesis of penicillins and cephalosporins (2,7,13,29,67,85,124). The molecular units that comprise penicillins and cephalosporins were known to be L-cysteine, L-valine, and an appropriate side-chain precursor.…”

Section: Biosynthesismentioning

confidence: 99%

“…The molecular units that comprise penicillins and cephalosporins were known to be L-cysteine, L-valine, and an appropriate side-chain precursor. Penam and cephem antibiotics can be classifi ed into two groups with regard to their biosynthetic patterns, which are designated as Penicillium type and Cephalosporium type (85). The Penicillium type leads to the production of penicillins with nonpolar acyl side chains derived from mono-substituted acetic acids.…”

Section: Biosynthesismentioning

confidence: 99%

Natural Beta-Lactam Antibiotics

Aoki¹,

Okuhara²

1980

Annu. Rev. Microbiol.

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“…This fungus was initially identified as a strain of Cephalosporium acremonium but later reclassified as Acremonium chrysogenum (Lemke and Brannon, 1972) and more recently as A. strictum (see Chapter 1). Advances in this area were slow because the activity was associated with a number of different types of compounds.…”

Section: Naturally Occurring Cephalosporinsmentioning

confidence: 99%

Penicillium and Acremonium

Peberdy¹

1987

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v Foreword Biotechnology is a word that was originally coined to describe the new processes which could be derived from our ability to manipulate, in vitro, the genetic material common to all organisms. I t has now become a generic term encompassing all "applications" of living systems, including the more traditional fermentation and agricultural industries. Recombinant DNA technology has opened up new opportunities for the exploitation of microorganisms and animal and plant cells as producers or modifiers of chemical and biological products.This series of handbooks deals exclusively with microorganisms which are at the forefront of the new technologies and brings together in each of its volumes the background information necessary to appreciate the historical development of the organisms making up a particular genus, the degree to which molecular biology has opened up new opportunities, and the place they occupy in today's biotechnology industry. Our aim was to make this primarily a practical approach, with emphasis on methodology, combining for the first time information which has largely been spread across a wide literature base or only touched upon briefly in review articles. Each handbook should provide the reader with a source text, from which the importance of the genus to his or her work can be identified, and a practical guide to the handling and exploitation of the organisms included.It is perhaps apt that Volume I of the series should deal with a group of organisms involved in producing chemicals which have dominated the fermentation and pharmaceutical industries for the past forty years-the antibiotics. In terms of the degree to which molecular biology has made an impact on this genus to date, it is clear that the major rewards are still to come.

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Microbial Synthesis of Cephalosporin and Penicillin Compounds

Cited by 23 publications

References 232 publications

Isolation and nature of intracellular alpha-aminoadipic acid-containing peptides from Paecilomyces persicinus P-10

Isolation and nature of intracellular alpha-aminoadipic acid-containing peptides from Paecilomyces persicinus P-10

Natural Beta-Lactam Antibiotics

Penicillium and Acremonium

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