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Cyclo(L-Phe-L-Pro)

Names

[ CAS No. ]:
3705-26-8

[ Name ]:
Cyclo(L-Phe-L-Pro)

[Synonym ]:
CYCLO-L-PHENYLALANYL-L-PROLINE
(3S,8aS)-3-Benzylhexahydropyrrolo[1,2-a]pyrazine-1,4-dione
(3S-trans)-3-Benzylhexahydropyrrolo(1,2-a)pyrazine-1,4-dione
Pyrrolo[1,2-a]pyrazine-1,4-dione, hexahydro-3-(phenylmethyl)-, (3S,8aS)-
Einecs 223-047-0

Biological Activity

[Description]:

Cyclo(L-Phe-L-Pro), isolated from Pseudomonas fluorescens and Pseudomonas alcaligenes cell-free culture supernatants is an antifungal cyclic dipeptide[1]. Cyclo(L-Phe-L-Pro) inhibits IFN-β production by interfering with retinoic-acid-inducible gene-I (RIG-I) activation[2]. Cyclo(L-Phe-L-Pro) exhibits free-radical scavenging activity with the IC50 of 24 µM in the DPPH assay[3].

[Related Catalog]:

Research Areas >> Cancer
Signaling Pathways >> Immunology/Inflammation >> IFNAR
Research Areas >> Infection
Signaling Pathways >> Anti-infection >> Fungal
Research Areas >> Inflammation/Immunology

[References]

[1]. Katrin Ström, et al. Lactobacillus plantarum MiLAB 393 Produces the Antifungal Cyclic Dipeptides Cyclo(L-Phe-L-Pro) and Cyclo(L-Phe-trans-4-OH-L-Pro) and 3-Phenyllactic Acid. Appl Environ Microbiol. 2002 Sep;68(9):4322-7.

[2]. Wooseong Lee, et al. Vibrio vulnificus quorum-sensing molecule cyclo(Phe-Pro) inhibits RIG-I-mediated antiviral innate immunity. Nat Commun. 2018 Apr 23;9(1):1606.

[3]. Keyong Ho Lee, et al. Radioprotective effect of cyclo(L-phenylalanyl-L-prolyl) on irradiated rat lung. J Microbiol Biotechnol. 2008 Feb;18(2):369-76.

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
509.5±39.0 °C at 760 mmHg

[ Molecular Formula ]:
C14H16N2O2

[ Molecular Weight ]:
244.289

[ Flash Point ]:
262.0±27.1 °C

[ Exact Mass ]:
244.121185

[ PSA ]:
49.41000

[ LogP ]:
-0.56

[ Vapour Pressure ]:
0.0±1.3 mmHg at 25°C

[ Index of Refraction ]:
1.614

[ Storage condition ]:
-15°C

Safety Information

[ Hazard Codes ]:
Xi

Related Compounds