Cyclo(L-prolinyl-L-tyrosine)

• CAT Number: R036299
• CAS Number: 4549-02-4
• Molecular Formula: C14H16N2O3
• Molecular Weight: 260.293
• Purity: ≥95%
• Synonyms: (3S,8aS)-Hexahydro-3-[(4-hydroxyphenyl)methyl]pyrrolo[1,2-a]pyrazine-1,4-dione; (3S-trans)-Hexahydro-3-[(4-hydroxyphenyl)methyl]-pyrrolo[1,2-a]pyrazine-1,4-dione; Hexahydro-3-(p-hydroxybenzyl)-pyrrolo[1,2-a]pyrazine-1,4-dione; Cyclo L-Prolyl-L-tyrosi
• Target: Disease Research Fields
• Storage: Store at RT
• IUPAC Name: (3S,8aS)-3-[(4-hydroxyphenyl)methyl]-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione
• InChI: InChI=1S/C14H16N2O3/c17-10-5-3-9(4-6-10)8-11-14(19)16-7-1-2-12(16)13(18)15-11/h3-6,11-12,17H,1-2,7-8H2,(H,15,18)/t11-,12-/m0/s1
• InChIKey: LSGOTAXPWMCUCK-RYUDHWBXSA-N
• SMILES: C1CC2C(=O)NC(C(=O)N2C1)CC3=CC=C(C=C3)O

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.
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.

Reference

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.