246
Views
3
CrossRef citations to date
0
Altmetric
Research Article

A new fermentation process allows large-scale production of tetra-N-acetyl-chitotetraosyl allosamizoline

, , &
Pages 597-599 | Received 01 Mar 2006, Accepted 08 Apr 2006, Published online: 04 Oct 2008

References

  • Tokoro A, Tatewaki N, Suzuki K, Mikami T, Suzuki S, Suzuki M. Growth-inhibitory effects of hexa-N-acetylchitohexaose and chitohexaose against Meth-A solid tumor. Chem Pharm Bull 1988; 36: 784–790
  • Kendra DF, Hadwiger LA. Characterization of the smallest chitosan oligomer that is maximally antifungal to. Fusarium solani and elicits pisatin from Pisum sativum. Exp Mycol 1984; 8: 276–281
  • Sakuda S, Isogai A, Matsumoto S, Suzuki A, Koseki K, Kodama H, Yamada Y. Absolute configuration of allosamizoline and aminocyclitol derivative of the chitinase inhibitor allosamidin. Agric Biol Chem 1988; 52: 1615–1618
  • Griffith DA, Danishefsky SJ. Total Synthesis of Allosamidin. An Application of the Sulfonamidoglycosylation of Glycals. J Am Chem Soc 1991; 113: 5863–5864
  • Berecibar A, Grandjean C, Siriwardena A. Synthesis and biological activity of natural aminocyclopentitol glycosidase inhibitors: Mannostatin, trehazolin, allosamidin and their analogues. Chem Rev 1999; 99: 779–844
  • Andersen OA, Dixon MJ, Eggleston IM. and van Aalten Daan MF. Natural product family 18 chitinase inhibitors. Nat Prod Rep 2005; 22: 563–579
  • Kamst E, Pilling J, Raamsdonk LM, Lugtenberg BJJ, Spaink HP. Rhizobium nodulation protein NodC is an important determinant of chitin oligosaccharide chain length in Nod factor biosynthesis. J Bacteriol 1997; 179: 2103–2108
  • Samain E, Drouillard S, Heyraud A, Driguez H, Geremia RA. Gram-scale synthesis of recombinant chitooligosaccharides in Escherichia coli. Carbohydr Res 1997; 302: 35–42
  • Huang GL, Zhang DW, Zhao HJ, Zhang HC, Wang PG. Chemo-enzymatic synthesis of allyl penta-N-acetyl-chitopentaose. Bioorg Med Chem Lett 2006; 16: 2042–2043
  • Huang GL, Zhang DW, Zhao HJ, Zhang HC, Wang PG. Chemo-enzymatic synthesis of 1,4-oxazepanyl sugar as potent inhibitor of chitinase. Bioorg Med Chem 2006; 14: 2446–2449
  • Blattner R, Furneaux RH, Kemmitt T, Tyler PC, Ferrier RJ, Tidén AK. Syntheses of the fungicide/insecticide allosamidin and a structural isomer. J Chem Soc, Perkin Trans 1994; 1: 3411–3421
  • Huang GL, Mei XY, Liu MX, Liu TC. Synthesis, (1 → 3)-beta-D-glucanase-binding ability and phytoalexin-elicitor activity of (R)-2,3-epoxypropyl (1 → 3)-beta-D-pentaglucoside. Bioorg Med Chem Lett 2004; 14: 6027–6029
  • Huang GL, Liu MX, Mei XY. Synthesis, (1 → 3)-beta-D-glucanase-binding ability, and phytoalexin-elicitor activity of a mixture of 3,4-epoxybutyl (1 → 3)-beta-D-oligoglucosides. Carbohydr Res 2004; 339: 1453–1457
  • Terwisscha van Scheltinga AC, Armand S, Kalk KH, Isogai A, Henrissat B, Dijkstra BW. Stereochemistry of chitin hydrolysis by a plant chitinase/lysozyme and X-ray structure of a complex with allosamidin: Evidence for substrate assisted catalysis. Biochemistry 1995; 34: 15619–15623
  • Terwisscha van Scheltinga AC, Kalk KH, Beintema JJ, Dijkstra BW. Crystal structure of hevamine, a plant defence protein with chitinase and lysozyme activity, and its complex with an inhibitor. Structure 1994; 2: 1181–1189

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.