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The chemical structure of sisomicin

Die chemische Struktur von Sisomicin

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Summary

Sisomicin, the principal antibiotic produced in the fermentation of Micromonospora inyoensis, has the chemical structure 0-2,6-diamino-2,3,4,6-tetradeoxy-a-D-glycero-hex-4-enopyranosyl (1→4)-0- [3-deoxy-4-C-methyl-3-(methylamino)-β-L-arabinopyranosyl (1→6)]-2-deoxy-D-streptamine. Sisomicin contains a novel unsaturated sugar unit, a structural feature not previously encountered in any aminocyclitol antibiotic.

Zusammenfassung

Sisomicin, ein Antibiotikum, das überwiegend bei der Fermentation von Micromonospora inyoensis entsteht, hat folgende chemische Struktur: 0-2,6-diamino-2,3,4,6-tetradeoxy-a-D-glycero-hex-4-enopyranosyl (1→4)-0-[3-deoxy-4-C-methyl-3-(methylamino)-β-L-arabinopyranosyl (1→6)]-2-deoxy-D-streptamine. Sisomicin enthält eine neue ungesättigte Zuckereinheit, eine Struktureigenschaft, die bisher bei keinem Aminocyclitol-Antibiotikum gefunden wurde.

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Literature

  1. Weinstein, M. J., Marquez, J. A., Testa, R. T., Wagman, G. H., Oden, E. M., Waitz, J. A. Antibiotic 6640, a new Micromonospora-produced aminoglycoside antibiotic. J. Antibiot. 23 (1970) 551–554.

    Google Scholar 

  2. Cooper, D. J., Daniels, P. J. L., Yudis, M. D., Marigliano, H. M., Cuthrie, R. D., Bukhari, S. T. K.: The gentamicin antibiotics. III: The gross structure of the gentamicin C components. J. Chem. Soc. (C) (1971) 3126–3129.

  3. Reimann, H., Cooper, D. J., Mallams, A. K., Jaret, R. S., Yehaskel, A., Kugelman, M., Vernay, H. F., Schumacher, D. The structure of sisomicin, a novel unsaturated aminocyclitol antibiotic from Micromonospora inyoensis. J. Org. Chem. 39 (1974) 1451–1457.

    Google Scholar 

  4. Cooper, D. J., Jaret, R. S., Reimann, H.: Structure of sisomicin, a novel unsaturated aminoglycoside antibiotic from Micromonospora inyoensis. Chem. Commun. (1971) 285–286.

  5. Reimann, H., Jaret, R. S., Cooper, D. J.: Sisomicin: Stereochemistry and attachment of the unsaturated sugar moiety. Chem. Commun. (1971) 924–925.

  6. Cooper, D. J., Yudis, M. D., Guthrie, R. D., Prior, A. M.: The gentamicin antibiotics. Part I. Structure and absolute stereochemistry of methyl garosaminide. J. Chem. Soc. (C) (1971) 960–963.

  7. Guthrie, R. D., Williams, G. J.: 2,6-Diamino-2, 3, 4, 6-tetradeoxy-D-threo-hexose (‘D-epi-purpurosamine’). Chem. Commun. (1971) 923–924.

  8. Kugelman, M., Mallams, A. K., Vernay, H. F. The preparation of garamine, a novel pseudodisaccharide from sisomicin. J. Antibiot. 26 (1973) 394–395.

    Google Scholar 

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Authors and Affiliations

  1. Research Division, Schering Corporation, 07003, Bloomfield, New Jersey, USA

    H. Reimann &  R. Jaret

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  1. H. Reimann
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  2. R. Jaret
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Reimann, H., Jaret, R. The chemical structure of sisomicin. Infection 4 (Suppl 4), S289–S291 (1976). https://doi.org/10.1007/BF01646952

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  • DOI: https://doi.org/10.1007/BF01646952

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