ChemicalBook--->CAS DataBase List--->2873-36-1

2873-36-1

2873-36-1 Structure

2873-36-1 Structure
IdentificationBack Directory
[Name]

CYCLO(-LEU-PRO)
[CAS]

2873-36-1
[Synonyms]

gancidinw
Maculosin 6
Cyclo(Pro-Leu)
CYCLO(-LEU-PRO)
cyclo-l-leu-l-pro
Cyclo(L-Pro-D-Leu)
Cyclo(L-Pro-L-Leu-)
Cyclo(proline-leucine)
Cyclo-L-prolyl-L-leucine
L-Leucyl-L-prolyl lactaM
Cyclo(L-prolyl-L-leucyl)
L-Leucyl-L-proline lactaM
Cyclo(L-leucyl-L-prolyl-)
Cyclo(-L-Leu-L-Pro)≥ 99% (TLC)
3-Isobutylhexahydropyrrolo[1,2-a]pyrazine-1,4-dione
(3S,8aS)-3-Isobutylhexahydropyrrolo[1,2-a]pyrazine-1,4-dione
(3S-trans)-hexahydro-3-isobutylpyrrolo[1,2-a]pyrazine-1,4-dione
2-a)pyrazine-1,4-dione,hexahydro-3-isobutyl-pyrrolo(stereoisomer
3-isobutyl-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-quinone
4-dione,hexahydro-3-(2-methylpropyl)-2-a)pyrazine-(3s-trans)-pyrrolo(
(3S,8aS)-Octahydro-3-(2-methylpropyl)pyrrolo[1,2-a]pyrazine-1,4-dione
(3S-trans)-Hexahydro-3-(2-Methylpropyl)-pyrrolo[1,2-a]pyrazine-1,4-dione
3-(2-methylpropyl)-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione
Pyrrolo[1,2-a]pyrazine-1,4-dione, hexahydro-3-(2-methylpropyl)-, (3S,8aS)-
(3S,8aS)-2,3,6,7,8,8a-Hexahydro-3-(2-methylpropyl)pyrrolo[1,2-a]pyrazine-1,4-dione
[EINECS(EC#)]

220-710-6
[Molecular Formula]

C11H18N2O2
[MDL Number]

MFCD00237617
[MOL File]

2873-36-1.mol
[Molecular Weight]

210.27
Chemical PropertiesBack Directory
[Melting point ]

163-165℃
[Boiling point ]

427.6±34.0 °C(Predicted)
[density ]

1.14
[storage temp. ]

Inert atmosphere,2-8°C
[solubility ]

Chloroform (Slightly), Ethanol (Slightly), Methanol (Slightly)
[form ]

Solid
[pka]

13.27±0.40(Predicted)
[color ]

White to Off-White
Hazard InformationBack Directory
[Description]

Cyclo(L-Leu-L-Pro) is a diketopiperazine metabolite that has been isolated from various bacterial and fungal species including Streptomyces. It is active against twelve strains of vancomycin-resistant enterococci (VRE) with MIC values of 12.5 μg/ml for E. faecalis strains K-99-34, K-00-184, and K-00-221. It also inhibits growth of K562, HL-60, and U937 leukemia cells in a concentration-dependent manner when used at concentrations of 1-500 μg/ml. Cyclo(L-Leu-L-Pro) also has antifouling activity, inhibiting attachment of B. amphitrite larva with an EC50 value of 0.15 mM.
[Chemical Properties]

White Solid
[Uses]

Sorbicillin analog. A bioactive secondary metabolites from terrestrial Streptomyces species TN262.
[Definition]

ChEBI: A homodetic cyclic peptide composed from leucyl and prolyl residues.
[References]

[1] RHEE K H. Isolation and characterization of Streptomyces sp KH-614 producing anti-VRE (vancomycin-resistant enterococci) antibiotics.[J]. Journal of General and Applied Microbiology, 2002, 48 6: 321-327. DOI: 10.2323/jgam.48.321
[2] XIANCUI LI. Antifouling diketopiperazines produced by a deep-sea bacterium, Streptomyces fungicidicus.[J]. Biofouling, 2006, 22 3-4: 201-208.
Safety DataBack Directory
[Toxicity]

mouse,LD50,intravenous,80mg/kg (80mg/kg),"Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978Vol. 2, Pg. 1354, 1978.
Spectrum DetailBack Directory
[Spectrum Detail]

CYCLO(-LEU-PRO)(2873-36-1)1HNMR
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