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The structure of sibirosamine — A new amino sugar from the antibiotic sibiromycin

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Summary

1. It has been shown that the antitumoral antibiotic sibiromycin is a glycoside of a new amino sugar which has been called sibirosamine.

2. It has been established that sibirosamine is a 3-C-methyl-4-methylamino-4,6-dideoxyhexopyranose, i.e., a new amino sugar differing from all the amino sugars known hitherto by the branching of the carbon skeleton.

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Literature cited

  1. 1.

    M. G. Brazhnikova, I. N. Kovsharova, N. V. Konstantinova, A. S. Mezentsev, V. V. Proshlyakova, and I. V. Tolstykh, Antibiotiki,4, 297 (1970).

  2. 2.

    W. Steglich and G. Höfle, Angew. Chem.,23, 1001 (1969).

  3. 3.

    H. Budzikiewicz, C. Djerassi, and D. Williams, Interpretation of Mass Spectra of Organic Compounds, Holden-Day, San Francisco (1964).

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Additional information

Institute for the Search for New Antibiotics, Academy of Medical Sciences of the USSR. S. Ordzhonikidze All-Union Chemical and Pharmaceutical Scientific-Research Institute. Translated from Khimiya Prirodnykh Soedineii, No. 5, pp. 650–654, September–October, 1971.

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Mezentsev, A.S., Kulyaeva, V.V., Rubasheva, L.M. et al. The structure of sibirosamine — A new amino sugar from the antibiotic sibiromycin. Chem Nat Compd 7, 629–632 (1971). https://doi.org/10.1007/BF00568425

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Keywords

  • Periodate
  • Acetic Anhydride
  • CD3OD
  • Amino Sugar
  • White Amorphous Powder