Biosynthesis of streptomycin. VI. myo-inosose-2, an intermediate in streptidine biosynthesis

Horner, William H.; Russ, Gerald A.

doi:10.1016/0304-4165(69)90376-6

Cited by 9 publications

(4 citation statements)

References 10 publications

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“…Assay of the specific activities of the streptidine moiety of the isolated streptomycin disclosed a 41 % reduction in those obtained from myo-inositol-supplemented cultures as compared to control cultures. More definitive information has recently been obtained by HORNER (1964b) who administered myo-inositol-U-14C to streptomycin-producing cultures. As much as a 29.5 % incorporation of isotope into streptomycin was observed (Table 6).…”

Section: Biosynthesis Of Streptidinementioning

confidence: 98%

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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Section: Biosynthesis Of Streptidinementioning

confidence: 98%

Biosynthesis

1967

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“…The biosynthetic pathway leading to streptomycin has been fully elucidated (187)(188)(189)(190)(191)(192)(193)(194)(195)(196)(197)(198)(199)(200)(201)(202)(203)(204)(205). WALKER and WALKER (193) showed that the streptidine moiety of streptomycin arises from myoinositol (80) incorporation of guanidine functions is achieved by arginine amidine transfer mediated by transamidinase.…”

Section: Streptomycin and Related Antibioticsmentioning

confidence: 99%

“…The presence of a phosphonic acid linked to an arginine N-methylhydrazined derivative in fosfazinomycins is unique. (190) The rhizocticins A (195), B (196), C (197) and D (198) are unusual diand tripeptides that were isolated from a Bacillus subtilis strain (404). The structure was elucidated by spectral analysis of the natural product and its 2-amino-3,5-dimethylpyrimidyl derivative (47); the absolute stereochemistry was established by its total synthesis from L-histidine, Larginine and dibromoethane (47).…”

Section: Macrocyclic Lactone Antibioticsmentioning

confidence: 99%

Some Aspects of Guanidine Secondary Metabolites

Berlinck

1995

Fortschritte Der Chemie Organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products

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“…The role of scyllo-inosose as a direct intermediate to scyllo-inosamine involved in streptidine biosynthesis was established by HORNER and Russ (1969 [2-14 C]inositol was fed to S.griseus. Streptomycin isolated after 24-h incubation was degraded to streptidine which was analyzed for 3H: 14 C ratio.…”

Section: Biosynthesis Of Subunits A) Streptidinementioning

confidence: 99%