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Chemical Compound Review

NSC-605157     4,6-diaminocyclohexane-1,2,3- triol...

Synonyms: NSC605157, AC1L73VF, AC1Q3F6J
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Disease relevance of Deoxystreptamine


High impact information on Deoxystreptamine

  • A comparative study of inhibition by different 2-deoxystreptamine analogues reveals structural features of the aminoglycoside antibiotics required for their interaction and effect on group I introns [5].
  • Substitution of the C-1 atom in the 2-deoxystreptamine moiety of gentamicin C2, a broad-spectrum aminoglycoside antibiotic, by an axial hydroxymethyl group has been reported to confer protection against most clinically important bacterial enzymes inactivating aminoglycosides, while simultaneously reducing the nephrotoxic potential of this drug [6].
  • The appearance of the enzyme in late-log phase, coupled with its narrow substrate specificity, indicates that it participates predominantly in 2-deoxystreptamine biosynthesis rather than in general metabolism [1].
  • Chromatographic analysis of fragments from the acid hydrolysis of these derivatives showed that the preferred site of acylation was in the 2-deoxystreptamine unit of the aminoglycosides [7].
  • Hygromycin B, which is a monosubstituted 2-deoxystreptamine-containing aminoglycoside, potently inhibited the elongation of nascent chains during the translation of polysomes [8].

Chemical compound and disease context of Deoxystreptamine


Biological context of Deoxystreptamine

  • A part of the new biosynthetic gene cluster for 2-deoxystreptamine-containing antibiotics was identified from Streptoalloteichus hindustanus [14].
  • The syntheses include four key steps, that is, transformation of 2-deoxystreptamine moiety of lividamine to 4-N,3-O-didemethyl-2-deoxyfortamine, selective 4-N-methylation of the new aminocyclitol moiety, selective attachment of a glycyl residue to the methylamino group at C-4 and selective amination at C-6' [15].

Anatomical context of Deoxystreptamine

  • The anomeric aminoglycosides, RU 21886 and RU 23468, which both have a 2-deoxystreptamine residue, stabilize 70S ribosomes to similar extents at low magnesium ion concentrations [16].

Associations of Deoxystreptamine with other chemical compounds


  1. Reactions catalyzed by purified L-glutamine: keto-scyllo-inositol aminotransferase, an enzyme required for biosynthesis of aminocyclitol antibiotics. Lucher, L.A., Chen, Y.M., Walker, J.B. Antimicrob. Agents Chemother. (1989) [Pubmed]
  2. Effect of tobramycin on protein synthesis in 2-deoxystreptamine aminoglycoside-resistant clinical isolates of Haemophilus influenzae. Levy, J., Burns, J.L., Mendelman, P.M., Wong, K., Mack, K., Smith, A.L. Antimicrob. Agents Chemother. (1986) [Pubmed]
  3. Photo-induced labelling of Escherichia coli ribosomes by a tobramycin analog. Tangy, F., Capmau, M.L., Le Goffic, F. Eur. J. Biochem. (1983) [Pubmed]
  4. Biosynthesis of 2-deoxystreptamine by three crucial enzymes in Streptomyces fradiae NBRC 12773. Kudo, F., Yamamoto, Y., Yokoyama, K., Eguchi, T., Kakinuma, K. J. Antibiot. (2005) [Pubmed]
  5. Non-competitive inhibition of group I intron RNA self-splicing by aminoglycoside antibiotics. von Ahsen, U., Davies, J., Schroeder, R. J. Mol. Biol. (1992) [Pubmed]
  6. New derivatives of kanamycin B obtained by combined modifications in positions 1 and 6". Synthesis, microbiological properties, and in vitro and computer-aided toxicological evaluation. Van Schepdael, A., Busson, R., Vanderhaeghe, H.J., Claes, P.J., Verbist, L., Mingeot-Leclercq, M.P., Brasseur, R., Tulkens, P.M. J. Med. Chem. (1991) [Pubmed]
  7. Aminoglycoside antibiotics. 6. Chemical reactions of aminoglycosides with disodium carbenicillin. Iyengar, B.S., Kumar, V., Wunz, T.P., Remers, W.A. J. Med. Chem. (1986) [Pubmed]
  8. Mechanisms of action of aminoglycoside antibiotics in eucaryotic protein synthesis. Eustice, D.C., Wilhelm, J.M. Antimicrob. Agents Chemother. (1984) [Pubmed]
  9. Production of antibiotic SU-2 complex by a 2-deoxystreptamine idiotroph of Micromonospora sagamiensis. Kase, H., Kitamura, S., Nakayama, K. J. Antibiot. (1982) [Pubmed]
  10. Confirmation of in vitro synthesis of 2-deoxy-scyllo-inosose, the earliest intermediate in the biosynthesis of 2-deoxystreptamine, using cell free preparations of Streptomyces fradiae. Yamauchi, N., Kakinuma, K. J. Antibiot. (1992) [Pubmed]
  11. Isolation and characterisation of an aminoglycoside phosphotransferase from neomycin-producing Micromonospora chalcea; comparison with that of Streptomyces fradiae and other producers of 4,6-disubstituted 2-deoxystreptamine antibiotics. Salauze, D., Davies, J. J. Antibiot. (1991) [Pubmed]
  12. Biotransformation, a new approach to aminoglycoside biosynthesis. I. Sisomicin. Testa, R.T., Tilley, B.C. J. Antibiot. (1975) [Pubmed]
  13. Mutational biosynthesis by idiotrophs of Micromonospora purpurea. II. Conversion of non-amino containing cyclitols to aminoglycoside antibiotics. Daum, S.J., Rosi, D., Goss, W.A. J. Antibiot. (1977) [Pubmed]
  14. Biosynthesis of 2-deoxystreptamine-containing antibiotics in Streptoalloteichus hindustanus JCM 3268: characterization of 2-deoxy-scyllo-inosose synthase. Hirayama, T., Tamegai, H., Kudo, F., Kojima, K., Kakinuma, K., Eguchi, T. J. Antibiot. (2006) [Pubmed]
  15. Syntheses of sporaricin analogues, 2-deoxy-4-N-glycyl-6-O-(alpha-nebrosaminyl)fortamine and its 3-de-O-methyl compound. Yamaguchi, T., Kyotani, Y., Watanabe, I., Sato, S., Takahashi, Y., Nagakura, M., Mori, T. J. Antibiot. (1979) [Pubmed]
  16. Stability of 70S ribosomes in relation to misreading and antibacterial activity of aminoglycosides. Cousin, M.A., Lando, D., Ojasoo, T., Raynaud, J.P. Biochimie (1977) [Pubmed]
  17. Susceptibility of Saccharomyces spp. and Schwanniomyces spp. to the aminoglycoside antibiotic G418. Panchal, C.J., Whitney, G.K., Stewart, G.G. Appl. Environ. Microbiol. (1984) [Pubmed]
  18. Crystallization and X-ray analysis of 2-deoxy-scyllo-inosose synthase, the key enzyme in the biosynthesis of 2-deoxystreptamine-containing aminoglycoside antibiotics. Nango, E., Kumasaka, T., Sato, T., Tanaka, N., Kakinuma, K., Eguchi, T. Acta Crystallograph. Sect. F Struct. Biol. Cryst. Commun. (2005) [Pubmed]
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