The biosynthesis of penicillin. 1. The incorporation of some amino acids into penicillin

Arnstein, H. R. V.; Grant, P. T.

doi:10.1042/bj0570353

Cited by 50 publications

(15 citation statements)

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“…Arnstein and Grant (3,4) demonstrated by incorporation studies with DL- [3-14C ]cystine and L-[3-14C ]cystine-15N-3_S that the intact cystine molecule was used for the biosynthesis of penicillin. They also noted that L-cystine was a better precursor than D-cystine.…”

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confidence: 99%

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Incorporation of Double-Labeled l -Cystine and dl -Valine in Penicillin

Adriaens

Vanderhaeghe

Meesschaert

et al. 1975

Antimicrob Agents Chemother

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L- [3,3'-3H ]cystine was incorporated into penicillin with retention of one.tritium. This result can be explained by ,l-lactam formation through ring closure between C3 of cysteine and NH of valine. No radioactivity of DL-[2,3-3H]valine was incorporated into penicillin. The loss of isotope at C2 occurs during the inversion of configuration. The loss of label at C3 is discussed in terms of possible intermediates for the formation of the thiazolidine ring of penicillin.

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confidence: 99%

“…Fermentations were carried out in the medium of Jarvis and Johnson (7). Fifty milliliters of this medium in 300-ml Erlenmeyer flasks were inoculated with 3 x 107 conidia from 6-day-old cultures on complete medium and incubated at 27 C and 300 rpm on a rotary shaker. After 48 h, the suspensions were filtered with suction on sterile Whatman no.…”

mentioning

confidence: 99%

Incorporation of Double-Labeled l -Cystine and dl -Valine in Penicillin

Adriaens

Vanderhaeghe

Meesschaert

et al. 1975

Antimicrob Agents Chemother

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“…Similarly, the 13C of(2S, 3S)-[4-13C]valine was incorporated exclusively into the exocyclic methylene of cephalosporin C at C-17 and that of (2 RS, 3 R)-[4-13 C]valine into the C-2 of cephalosporins (KLUENDER et al, 1973). Labeled cysteine was found to be incorporated into benzylpenicillin in P. chrysogenum (ARNSTEIN and GRANT, 1954), into cephalosporin C in C. acremonium (TROWN et al, 1963), and into cephamycin C in S. clavuligerus (WHITNEY et al, 1972). Labeled cysteine was found to be incorporated into benzylpenicillin in P. chrysogenum (ARNSTEIN and GRANT, 1954), into cephalosporin C in C. acremonium (TROWN et al, 1963), and into cephamycin C in S. clavuligerus (WHITNEY et al, 1972).…”

Section: B Valinementioning

confidence: 98%

Biosynthesis

1981

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“…The feeding of [4 14 C]-oL-valine to P. chrysogenum first demonstrated the incorporation of this amino acid into benzylpenicillin (Arnstein and Grant, 1954). Later examination of the relative rates of incorporation of 0-and L-[I-14 C] valine indicated that L-valine was more rapidly taken up by the mycellium and used for penicillin biosynthesis (Stevens and De Long, 1958;.…”

Section: Incorporation Of Valine and Cyst(e)ine Into Penicillins And mentioning

confidence: 99%

“…Similar experiments using the deuteriumlabeled chiral valines and mass spectrometric analysis of penicillin N supported the conclusions described above, but in addition established that all the original methyl hydrogens of valine remain intact in penicillin biosynthesis (Kluenderetal.,1974). The first significant radiochemical experiments to demonstrate that the fJ-Iactam ring is derived from cyst(e)ine were conducted in the early 1950s (Arnstein and Grant, 1954). To establish whether cyst(e)ine was incorporated intact, triply labeled [3_ 14 C]-, [15N ]-, [ 35 S ]-D-and L-cystine were fed to P. chrysogenum.…”

Section: Incorporation Of Valine and Cyst(e)ine Into Penicillins And mentioning

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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The biosynthesis of penicillin. 1. The incorporation of some amino acids into penicillin

Cited by 50 publications

References 15 publications

Incorporation of Double-Labeled l -Cystine and dl -Valine in Penicillin

Incorporation of Double-Labeled l -Cystine and dl -Valine in Penicillin

Biosynthesis

Penicillium and Acremonium

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