Cyclo(L-Pro-L-Tyr) (maculosin) is a diketopiperazine formed by the fusion of tyrosine and proline, reported as a secondary metabolite of fungi and bacteria. In Pseudomonas aeruginosa, cyclo(L-Pro-L-Tyr) is capable of activating N-acylhomoserine lactones (AHLs). Cyclo(L-Pro-L-Tyr) is also capable of activating or antagonizing other LuxR-based quorum-sensing systems. Cyclo(L-Pro-L-Tyr) was identified as a host-specific toxin produced by Alternaria alternata on spotted knapweed.
Cyclo(L-Pro-L-Tyr) is soluble in ethanol, methanol, DMF or DMSO. Limited water solubility.
Cyclo(L-Pro-L-Tyr) is soluble in ethanol, methanol, DMF or DMSO. Limited water solubility.
| Mechanism of Action | While the mode of action of cyclo(L-Pro-L-Tyr) is not known, its activity suggests the existence of cross talk among bacterial signalling systems. |
| Molecular Formula | C14H16N2O3 |
| References | Citromycetins and bilains A-C: new aromatic polyketides and diketopiperazines from Australian marinederived and terrestrial Penicillium spp. Capon R.J. et al. J. Nat. Prod. 2007, 70, 1746. Quorum-sensing cross talk: isolation and chemical characterization of cyclic dipeptides from Pseudomonas aeruginosa and other Gram-negative bacteria. Holden, M.T.G. et al. Mol. Microbiol. 1999, 33, 1254. Maculosin, a host-specific phytotoxin for spotted knapweed from Alternaria alternata. Stierle A.C. Proc. Natl. Acad. Sci. USA 1988, 85, 8008. |
