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Chemical Compound Review

Polyoxin     1-[(2R,3R,4S,5R)-5-(1-amino- 2-oxo-ethyl)-3...

Synonyms: Polyoxins, LS-118149, AC1MJ1W3, C23H32N6O14, 11113-80-7
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Disease relevance of Polyoxins

  • This aminoaldonic acid is the N terminus of the nucleoside peptide antibiotics, the polyoxins, produced by Streptomyces cacaoi var. asoensis [1].

High impact information on Polyoxins

  • Chitin synthase inhibitors have been studied through chemical modification of the polyoxins and nikkomycins but are limited because of unfavorable pharmacokinetics [2].
  • The activity also had a pH optimum of 7.5, was most stimulated by Mg(2+), and was more inhibited by polyoxin D than by nikkomycin Z [3].
  • The synthesis and biological properties of seven polyoxins (4-10) designed to avoid peptidase hydrolysis in Candida albicans are presented [4].
  • At concentrations up to 2 mM these two new polyoxins were ineffective in the inhibition of cell growth or reduction of cell viability, but they induced aberrant morphologies in C. albicans at a concentration of 0.25 mM [5].
  • Five dipeptidyl and two tripeptidyl polyoxin analogues were synthesized by coupling an amino acid active ester or azlactone to uracil polyoxin C (2) or polyoxin D (1), subsequent removal of the protecting group, and purification by preparative HPLC [4].

Chemical compound and disease context of Polyoxins


Biological context of Polyoxins

  • These data suggest that polyoxins containing hydrophobic amino acids retain strong chitin synthetase inhibitory activity and are resistant to cellular hydrolysis [5].
  • Chitin synthetase was competitively inhibited by polyoxin D (Ki 6.5 muM) and (Ki 1.35 mM), the latter giving complex kinetics [7].
  • These results demonstrated that the morphological alterations caused by polyoxin D were due to the absence of chitin, a wall component important for formation of primary septa and for maintenance of structural integrity during morphogenesis [8].
  • The most widely studied chitin synthase inhibitors are polyoxins and nikkomycins that probably bind to the catalytic site of chitin synthases [9].

Anatomical context of Polyoxins


Associations of Polyoxins with other chemical compounds

  • Chs2 also shows less sensitivity than Chs1 to inhibition by polyoxin D or sodium chloride, a property that was used to demonstrate the presence of Chs2 in wild-type extracts [14].
  • 1. Diflubenzuron and polyoxin D clearly inhibited the incorporation of [3H]-N-acetylglucosamine ([3H]NAGA) into chitin in the isolated integument from newly molted American cockroaches under the experimental condition [15].

Gene context of Polyoxins

  • Larvae fed on the potent chitin synthase inhibitor polyoxin D or the chitin-binding agent Calcofluor White, showed strong concentration-dependent inhibition of larval weight and survival but no discernible effects on the matrix structure [16].
  • The polyoxins and other structurally-related antibiotics like nikkomycins are strong competitive inhibitors of the polymerizing enzyme chitin synthase [17].

Analytical, diagnostic and therapeutic context of Polyoxins


  1. Biosynthesis of the polyoxins, nucleoside peptide antibiotics: glutamate as an origin of 2-amino-2-deoxy-L-xylonic acid (polyoxamic acid). Funayama, S., Isono, K. Biochemistry (1975) [Pubmed]
  2. Antibiotics that inhibit fungal cell wall development. Debono, M., Gordee, R.S. Annu. Rev. Microbiol. (1994) [Pubmed]
  3. WdChs4p, a homolog of chitin synthase 3 in Saccharomyces cerevisiae, alone cannot support growth of Wangiella (Exophiala) dermatitidis at the temperature of infection. Wang, Z., Zheng, L., Hauser, M., Becker, J.M., Szaniszlo, P.J. Infect. Immun. (1999) [Pubmed]
  4. Synthesis and biological properties of chitin synthetase inhibitors resistant to cellular peptidases. Shenbagamurthi, P., Smith, H.A., Becker, J.M., Naider, F. J. Med. Chem. (1986) [Pubmed]
  5. Hydrophobic polyoxins are resistant to intracellular degradation in Candida albicans. Smith, H.A., Shenbagamurthi, P., Naider, F., Kundu, B., Becker, J.M. Antimicrob. Agents Chemother. (1986) [Pubmed]
  6. Stereospecificity of the enzymatic dehydrogenation in the biosynthesis of 3-ethylidene-L-azetidine-2-carboxylic acid from isoleucine by Streptomyces cacaoi. Hill, R.K., Rhee, S.W., Isono, K., Crout, D.H., Suhadolnik, R.J. Biochemistry (1981) [Pubmed]
  7. Synthesis of chitin by particulate preparations from Aspergillus flavus. López-Romero, E., Ruiz-Herrara, J. Antonie Van Leeuwenhoek (1976) [Pubmed]
  8. Polyoxin D inhibits colloidal gold-wheat germ agglutinin labelling of chitin in dimorphic forms of Candida albicans. Hilenski, L.L., Naider, F., Becker, J.M. J. Gen. Microbiol. (1986) [Pubmed]
  9. Chitin synthesis as target for antifungal drugs. Ruiz-Herrera, J., San-Blas, G. Current drug targets. Infectious disorders. (2003) [Pubmed]
  10. Inhibition of chitin synthesis in the cell wall of Coccidioides immitis by polyoxin D. Hector, R.F., Pappagianis, D. J. Bacteriol. (1983) [Pubmed]
  11. Timing and function of chitin synthesis in yeast. Cabib, E., Bowers, B. J. Bacteriol. (1975) [Pubmed]
  12. Effects of polyoxin D on germination, morphological development and biosynthesis of the cell wall of Trichoderma viride. Benìtez, T., Villa, T.G., Acha, I.G. Arch. Microbiol. (1976) [Pubmed]
  13. Adhesion of Candida albicans to epithelial cells effect of polyoxin D. Gottlieb, S., Altboum, Z., Savage, D.C., Segal, E. Mycopathologia (1991) [Pubmed]
  14. Chitin synthetase 2, a presumptive participant in septum formation in Saccharomyces cerevisiae. Sburlati, A., Cabib, E. J. Biol. Chem. (1986) [Pubmed]
  15. Effect of diflubenzuron on incorporation of [3H]-N-acetylglucosamine ([3H]NAGA) into chitin in the intact integument from the newly molted American cockroach Periplaneta americana. Nakagawa, Y., Matsumura, F., Hashino, Y. Comp. Biochem. Physiol. C, Comp. Pharmacol. Toxicol. (1993) [Pubmed]
  16. Chitin is only a minor component of the peritrophic matrix from larvae of Lucilia cuprina. Tellam, R.L., Eisemann, C. Insect Biochem. Mol. Biol. (2000) [Pubmed]
  17. Chitin synthesis and degradation as targets for pesticide action. Cohen, E. Arch. Insect Biochem. Physiol. (1993) [Pubmed]
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