Incorporation of sarcosine into the actinomycins synthesized by <i>Streptomyces antibioticus</i>

Ciferri, Orio; Albertini, Alessandra M.; Cassani, Giovanni

doi:10.1042/bj0900082

Cited by 24 publications

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“…1) (23) (methionine, tryptophan, proline, valine, threonine, and glycine) were incorporated to some extent, varying between 8-and 86-pmol equivalents of radioactive actinomycin Iture age after 1 h of incubation and between 13.2-and (personal 170-pmol equivalents after 2 h. These differlasts was ences in incorporation may reflect differences ozyme in in the intracellular pool concentrations of the ium har-various amino acids, in the rates of entry of iarticular the amino acids into the protoplasts, and in 3t forma-the metabolic requirements of the organism ith myce-for specific amino acid substrates. Sarcosine, res; how-which can be incorporated into actinomycin by up to 3.5 mycelium of S. antibioticus (7,8) and S. parlasts was vulus (see below), and lysine, which is not an actinomycin precursor, were not incorporated.…”

Section: Resultsmentioning

confidence: 99%

Actinomycin Biosynthesis by Protoplasts Derived from Streptomyces parvulus

Hitchcock

Katz

1978

Antimicrob Agents Chemother

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Conditions are described for the formation of protoplasts from StreptomyceS. parvulus that are able to synthesize actinomycin D de novo. Antibiotic synthesis by protoplasts, in contrast to that by mycelium, was sensitive to inhibition by actinomycin D and to a decrease in sucrose concentration. On the other hand, synthesis by mycelium was much more sensitive to inhibition by amino acid analogs (D-valine, cis-3-methylproline, and a-methyl-DL-tryptophan). In addition, the uptake of amino acids (L-methionine, sarcosine, and L-and D-valine) by protoplasts was significantly lower than that by mycelium. The advantages and limitations of using protoplasts for studying in vivo actinomycin synthesis are discussed.

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Section: Resultsmentioning

confidence: 99%

Actinomycin Biosynthesis by Protoplasts Derived from Streptomyces parvulus

Hitchcock

Katz

1978

Antimicrob Agents Chemother

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“…The experiments with sarcosine-p4C revealed that the radioactivity of the carboxyl carbon of sarcosine was incorporated into the sarcosine of the antibiotic (KATZ and WEISSBACH, 1963;CIFERRI, ALBERTINI and ROSSI, 1962;CIFERRI, ALBERTINI and CASSANI, 1964). However, it was not established whether this occurs by a direct incorporation of the N-methylamino acid or by an initial conversion of sarcosine via a demethylation reaction to glycine which is then incorporated into the antibiotic peptide where the methylation reaction occurs.…”

Section: Biosynthesis Of Sarcosine N-methyl-l-valine and N-methylalamentioning

confidence: 93%

Biosynthesis

1967

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All rights, especially that of translation into f oreign 1anguages, reserved. It is also forbidden to reproduce this book, either who1e or in part, by photomechanical means (photostat, microfilm and/or microcard) or by other procedure without written pennission from Springcr-Vcrlag Berlin Heide1bCig GmbH. DedicationFor most areas of scientific pursuit, there is usually that rare investigator who has the imagination to conceive ideas, who has faith in his visions, and who has the ability to critically test his concepts in the laboratory. Almost invariably, this scientist also inspires younger men to enthusiastically enter into his research program. To him should go the accolades and the recognitions of the esteem in which he is held. As only a small part of this esteem, we wish to dedicate these books to Professor SELMAN A. W AKSMAN in appreciation of his leadership and contributions in all facets of antibiotic research. PrefaceThe idea for publishing these books on the mechanism of action and on the biosynthesis of antibiotics was born of frustration in our attempts to keep abreast of the literature. Gone were the years when we were able to keep a bibliography on antibiotics and feel confident that we could find everything that was being published on this sUbject. These fields of investigation were moving forward so rapidly and were encompassing so wide a range of specialized areas in microbiology and chemistry that it was almost impossible to keep abreast of developments. In our naivete and enthusiasm, however, we were unaware that we were toying with an idea that might enmesh us, that we were creating an entity with a life of its own, that we were letting loose a Golom who instead of being our servant would be our master.That we set up ideals for these books is obvious; they would be current guides to developments and information in the areas of mechanism of action and biosynthesis of antibiotics. For almost every subject, we wished to enlist the aid of an investigator who himself had played a part in determining the nature of the phenomena that were being discussed. One concept for the books was that they include only antibiotics for which a definitive, well-documented mechanism of action or biosynthetic pathway was known. Yet, such an approach would not entirely serve the purpose we projected, for it would not encompass all of the information available in these fields of antibiotic investigations and blind searches for the original literature would still have to be made. We therefore chose to include any and all antibiotics about which some pertinent information had been published. It was obvious even at the start that such a compilation, integration, and analysis of information could never be complete unless scientific investigations ceased at the moment the last manuscript was submitted-an end that was neither desirable nor possible. An addendum was therefore included at the end of the volume and left open for the addition of new information until the last pages of the regular articles had been printed.The...

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“…It has been reported (Katz & Weissbach, 1963;Ciferri, Albertini & Cassani, 1964) that when sarcosine is supplied to growing cultures of Strepto-myce8 antibioticu8 the amino acid is utilized as a source of the sarcosine moiety of the actinomycins. In addition, experiments with methyl-labelled sarcosine have indicated that sarcosine is incorporated without degradation.…”

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confidence: 99%

“…In addition to Streptomyces antibioticue strain no. 1692 (Ciferri et al 1964), an unidentified species, Streptomyces sp. V-187, was employed.…”

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Origin of the sarcosine molecules of actinomycins

Ciferri¹,

Albertini²,

Cassani³

1965

Biochemical Journal

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1. Streptomyces V-187 produces on minimal medium a mixture composed mainly of actinomycin C(1) (actinomycin D) and actinomycin A(1) (actinomycin I). If sarcosine is added to the medium, the micro-organism produces, in addition to actinomycins C(1) and A(1), actinomycin F(8) (actinomycin II) and actinomycin F(9) (actinomycin (III), characterized by the substitution by sarcosine of one or both the proline molecules present in actinomycin C(1). 2. Exogenous sarcosine seems to be incorporated as such by Streptomyces V-187 only in the sarcosine molecule(s) that replace proline in the actinomycins of the F group, whereas, for the synthesis of the other sarcosine molecules, the amino acid is first demethylated to glycine. 3. The incorporation of sarcosine and glycine into actinomycin by Streptomyces antibioticus appears to follow a similar pattern, except that a portion of the methyl group produced in the degradation of sarcosine is utilized as a source of the methyl groups of the antibiotic. This explains the previously reported lack of cross-dilution between glycine and sarcosine observed in the incorporation of these amino acids into actinomycin.

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Incorporation of sarcosine into the actinomycins synthesized by Streptomyces antibioticus

Cited by 24 publications

References 20 publications

Actinomycin Biosynthesis by Protoplasts Derived from Streptomyces parvulus

Actinomycin Biosynthesis by Protoplasts Derived from Streptomyces parvulus

Biosynthesis

Origin of the sarcosine molecules of actinomycins

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