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TUNICAMYCIN Basic information
TUNICAMYCIN Chemical Properties
  • Melting point:234-235℃ (decomposition)
  • alpha D20 +52° (c = 0.5 in pyridine)
  • Flash point:87℃
  • storage temp. 2-8°C
  • solubility Soluble in methanol, ethanol, DMSO, or DMF
  • form White to off-white solid
  • Sensitive Moisture & Light Sensitive
  • BRN 6888090
  • EPA Substance Registry SystemTunicamycin (11089-65-9)
Safety Information
  • Hazard Codes T+,T
  • Risk Statements 28
  • Safety Statements 28-37/39-45
  • RIDADR UN 3462 6.1/PG 2
  • WGK Germany 3
  • RTECS YO7980200
  • 8-10-18-21
  • HazardClass 6.1(a)
  • PackingGroup II
  • HS Code 29419090
TUNICAMYCIN Usage And Synthesis
  • Chemical PropertiesWhite solid
  • UsesThe tunicamycins are a family of lipophilic nucleosides with fatty acids conjugated to an aminoglycoside group. The complex comprises analogues, tunicamycins I to X. This composition is typical of other products less precisely described as tunicamycins A to D. The tunicamycins act by blocking the formation of N-glycoside linkages to proteins via inhibition of formation of dolichol monophosphate from N-acetylglucosamine-1-phosphate. Tunicamycin blocks the synthesis of all N-linked glycoproteins (N-glycans) and causes cell cycle arrest in G1 phase. Tunicamycins are broadly active against prokaryotes, eukaryotes and viruses.
  • UsesAs a tool in studying glycoproteins in a wide variety of biological systems.
  • DefinitionChEBI: A mixture of antiviral nucleoside antibiotics produced by Streptomyces lysosuperificus. It contains at least 10 homologues comprising uracil, N-acetylglucosamine, an 11-carbon aminodialdose called tunicamine, and a fatty aci linked to the amino group of the tunicamine. The homologues vary in the composition of the fatty acid moiety.
  • Purification MethodsThe components of this nucleotide antibiotic from Streptomyces sp. are purified by recrystallising 3 times from hot glass-distilled MeOH, and the white crystals are dissolved in 25% aqueous MeOH and separated on a Partisil ODS-10_ column (9.4 x 25 cm) [Magnum-9 Whatman] using a 260nm detector. The column is eluted with MeOH/H2O mixture adjusted to 1:4 (v/v) then to 2:4 (v/v). The individual components are recovered and lyophilised. Ten components have been isolated, and all were active (to varying extents) depending on the lengths of the aliphatic side-chains. The mixture has UV max at 205 and 260nm (A 1cm 230 and 110). It is stable in H2O at neutral pH but unstable in acidic solution. It inhibits protein glycosylation. [Mahoney & Duskin J Biol Chem 254 6572 1979, Elnein Trends Biochem Sci 6 219 1981, Takatsuki J Antibiot 24 215 1971.] Uracil, uridine and uridine nucleotides. These are resolved by ion-exchange chromatography with AG1 (Cl form). [Lindsay et al. Anal Biochem 24 506 1968.]
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