Cyclo(L-prolyl-L-valyl)

• CAT Number: R029215
• CAS Number: 2854-40-2
• Molecular Formula: C10H16N2O2
• Molecular Weight: 196.25
• Purity: 98%
• Synonyms: (3S-trans)-Hexahydro-3-(1-methylethyl)-pyrrolo[1,2-a]pyrazine-1,4-dione;?(S,S)-Hexahydro-3-isopropyl-pyrrolo[1,2-a]pyrazine-1,4-dione; (-)-(6S,9S)-Cyclo(prolylvalyl); Cyclo(L-Pro-L-Val); Cyclo(L-Val-L-Pro); Cyclo(L-prolyl-L-valine); Cyclo(L-prolyl-L-
• Target: Bacterial
• Appearance: White solid
• Storage: -20°C
• Analysis method: HPLC
• IUPAC Name: (3S,8aS)-3-propan-2-yl-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione
• InChI: InChI=1S/C10H16N2O2/c1-6(2)8-10(14)12-5-3-4-7(12)9(13)11-8/h6-8H,3-5H2,1-2H3,(H,11,13)/t7-,8-/m0/s1
• InChIKey: XLUAWXQORJEMBD-YUMQZZPRSA-N
• SMILES: CC(C)C1C(=O)N2CCCC2C(=O)N1

Cyclo(L-Pro-L-Val) is a diketopiperazine formed by the fusion of valine and proline, reported as a secondary metabolite of fungi and bacteria. In Pseudomonas aeruginosa, cyclo(L-Pro-L-Val) is capable of activating N-acylhomoserine lactones (AHLs). Cyclo(L-Pro-L-Val) is also capable of activating or antagonizing other LuxR-based quorum-sensing systems.
While the mode of action of the cyclo(L-Pro-L-Val) 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.