Terreic acid

Terreic acid

$90.00 - 1 mg

$315.00 - 5 mg

All prices in Australian dollars

Code
BIA-T1695
Synonyms
(-)-Terreic acid
CAS #
121-40-4
Molecular Formula
C7H6O4
Molecular Weight
154.12
Purity
>95% by HPLC
Long Term Storage
-20°C
Solubility
Soluble in ethanol, methanol, DMF or DMSO.

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Product Data Sheet

Application Notes

Terreic acid is a hemiquinone isolated as an antibacterial metabolite by Abraham and Florey in 1949. The stereochemistry of terreic acid was resolved by Miller in 1968. Terreic acid possesses broad Gram positive and Gram negative activity. Terreic acid is biosynthesised from 6-methylsalicylic acid and acts as a covalent inhibitor of the bacterial cell wall biosynthetic enzyme, MurA. Recently, terreic acid has been shown to bind to the acetyltransferase domain of a bifunctional enzyme, N-acetylglucosamine-1-phosphate-uridyltransferase/glucosamine-1-phosphate-acetyltransferase (GlmU), in Escherichia coli.

References

  • Abraham E. P. and Florey H. W., in Antibiotics, Florey H.W. et al., eds. Oxford University Press, New York, N. Y., 1949, Vol. I, 337.
  • The structure of terremutin. Miller M.W., Tetrahedron 1968, 24, 4839.
  • The fungal product terreic acid is a covalent inhibitor of the bacterial cell wall biosynthetic enzyme UDPN-acetylglucosamine 1-carboxyvinyltransferase (MurA). Huijong H. et al., Biochem. 2010, 49, 4276.
  • Escherichia coli N-acetylglucosamine-1-phosphate-uridyltransferase/glucosamine-1-phosphate-cetyltransferase (GlmU) inhibitory activity of terreic cid isolated from Aspergillus terreus. Sharma R. et al., J. Biomol. Screen. 2016, 21, 342.

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