Biosynthesis of Cephalosporins

Kanzaki, Toshihiko; Fujisawa, Yukio

doi:10.1016/s0065-2164(08)70112-6

Cited by 17 publications

(10 citation statements)

References 107 publications

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“…In fact, only a few penicillin N-producing strains synthesize cephalosporins. Interestingly, this relationship also holds true for mutants of Cephalosporium species (LEMKE and NASH 1972;KANZAKI and FUJISAWA 1976).…”

Section: A Chrysogenum)mentioning

confidence: 76%

“…po I ya leurum TUBAKI (1973) Arachnom yces minimus KITANO et al (1975KITANO et al ( , 1977 Anixiopsis peruviana KITANO et al (1975KITANO et al ( , 1977 Spiroidium fuscum KITANO et al (1975KITANO et al ( , 1977 Paecilomyces persicinus PISANO and VELLOZZI (1974) Paecilomyces carneus HIGGENS et al (1974) HO KITANO et al (1975) PISANO and VELLOZZI (1974) HIGGENS et al (1974) KANZAKI et al (1974KANZAKI and FUJISAWA (1976) TRAXLER et al (1975) FUJISAWA and KANzAKI(1975 a Most strains which produce deacetoxycephalosporin C also produce cephalosporin C and deacetylcephalosporin C tf.l ~.…”

Section: A Chrysogenum)mentioning

confidence: 99%

“…1011, produced a cephem compound F-2 (Table 2) in a culture broth (KANZAKI and FUJISAWA 1976). The compound F-2 was determined to be a Bunte salt, in which the O-acetyl group of cephalosporin C was replaced by thiosulfate nonbiologically (DEMAIN et al 1963).…”

Section: A Chrysogenum)mentioning

confidence: 99%

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Strain Improvement and Preservation of β-Lactam-Producing Microorganisms

Elander¹

1983

Antibiotics

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Section: A Chrysogenum)mentioning

confidence: 76%

Section: A Chrysogenum)mentioning

confidence: 99%

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Strain Improvement and Preservation of β-Lactam-Producing Microorganisms

Elander¹

1983

Antibiotics

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“…Addition of a variety of side-chain precursors to the fermentation medium resulted in the production of corre sponding penicillins (16,18). Natural penicillins (Table 1) are produced by either true fungi (eukaryote) (67,76) or Streptomyces (prokaryote) (67). For a long time only a few strains of molds had been known to produce ceph alosporin C. Recent studies using ,8-lactam-super-susceptible mutants of bacteria (72,74,77) have demonstrated, however, that a considerable num ber of genera of eukaryotic fungi other than Cephalosporium or Emericel [opsis produce cephalosporin C and related compounds.…”

Section: Occurrence Of Penicillins and Cephalosporinsmentioning

confidence: 99%

Natural Beta-Lactam Antibiotics

Aoki¹,

Okuhara²

1980

Annu. Rev. Microbiol.

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“…We also wanted to determine whether the dimer of LLD-tripeptide, i.e., bis[S-(L-a-aminoadipyl)-L-cysteinyl-D-valine]disulfide, could be converted to isopenicillin N. This dimer is known to be produced by certain blocked mutants of C. acremonium (5) 36255). The parental culture produces both cephalosporin C and penicillin N. Media and culture conditions.…”

mentioning

confidence: 99%

Cell-free cyclization of delta-(L-alpha-aminoadipyl)-L-cysteinyl-D-valine to isopenicillin N

Sawada¹,

Baldwin²,

Singh³

et al. 1980

Antimicrob Agents Chemother

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Cell-free cyclization of S-(L-a-aminoadipyl)-L-cysteinyl-D-valine to isopenicillin N by lytic enzyme extracts of Cephalosporium acremonium M-0198 was stimulated by ferrous ions. The optimum concentration of FeSO4 was 80 ,uM. No additional stimulation was observed with ascorbate, adenosine 5'-triphosphate, or a-ketoglutarate, but Triton X-100 and sonication of the extracts increased activity. ZnSO4 was very inhibitory to enzyme activity; CUSO4 was somewhat less inhibitory, and the least effective of the three was MnCl2. The dimer of the tripeptide was converted to a penicillin that has the biological spectrum of isopenicillin N, and this reaction was also stimulated by FeSO4. We found that sonication can be used directly to prepare extracts with cyclization activity from mycelia, without preparing protoplast lysates. The kinetics of cyclase appearance and disappearance during fermentation were similar to those of ring-expansion activity, i.e., enzyme appeared and peaked 13 h after growth ceased and then disappeared.Both our group (7) and Abraham's group (9) have shown, independently, that 6-(L-a(aminoadipyl)-L-cysteinyl-D-valine (LLD-tripeptide) is cyclized to isopenicillin N by extracts of Cephalosporium acremonium (Fig. 1). O'Sullivan et al. (9) isolated the product of the cell-free conversion and determined that the side chain of the penicillin was L-a-aminoadipic acid. Because oxidation of deacetoxycephalosporin C to deacetylcephalosporin C is stimulated by ferrous ions, ascorbate, and a-ketoglutarate (12) and because oxidative ring-expansion of penicillin N to deacetoxycephalosporin C is stimulated by ferrous ions and ascorbate (4, 10) we checked the effect of these additives on the oxidative ring-closure reaction. We also tested the effect of Triton X-100, which, we found, stimulates ring-expansion by these same cell-free extracts (11).We also wanted to determine whether the dimer of LLD-tripeptide, i.e., bis[S-(L-a-aminoadipyl)-L-cysteinyl-D-valine]disulfide, could be converted to isopenicillin N. This dimer is known to be produced by certain blocked mutants of C. acremonium (5)

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Biosynthesis of Cephalosporins

Cited by 17 publications

References 107 publications

Strain Improvement and Preservation of β-Lactam-Producing Microorganisms

Strain Improvement and Preservation of β-Lactam-Producing Microorganisms

Natural Beta-Lactam Antibiotics

Cell-free cyclization of delta-(L-alpha-aminoadipyl)-L-cysteinyl-D-valine to isopenicillin N

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