Cyclo(-leu-pro)

Names

[ Name ]:
Cyclo(-leu-pro)

[Synonym ]:
Gancidin W
CYCLO(L-LEU-L-PRO)
(3S-trans)-Hexahydro-3-isobutylpyrrolo(1,2-a)pyrazine-1,4-dione
Pyrrolo[1,2-a]pyrazine-1,4-dione, hexahydro-3-(2-methylpropyl)-, (3S,8aS)-
cyclo-L-Leu-L-Pro
EINECS 220-710-6
(3S,8aS)-3-Isobutylhexahydropyrrolo[1,2-a]pyrazine-1,4-dione
Cyclo(-Leu-Pro)

Biological Activity

[Description]:

Cyclo(L-Leu-L-Pro) is an inhibitory substance targeting to production of norsolorinic acid (NA，a precursor of aflatoxin)，which can be isolated from A. xylosoxidans NFRI-A1. Cyclo(L-Leu-L-Pro) inhibits accumulation of NA by A. parasiticus NFRI-95 and inhibits spore formation. Cyclo(L-Leu-L-Pro) inhibits aflatoxin production with an IC50 of 0.2 mg/mL in A. parasiticus SYS-4[1].

[Related Catalog]:

Research Areas >> Infection

Signaling Pathways >> Anti-infection >> Fungal

[References]

[1]. Yan PS, et al. Cyclo(L-leucyl-L-prolyl) produced by Achromobacter xylosoxidans inhibits aflatoxin production by Aspergillus parasiticus. Appl Environ Microbiol. 2004 Dec;70(12):7466-73.

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
427.6±34.0 °C at 760 mmHg

[ Melting Point ]:
163-165ºC

[ Molecular Formula ]:
C₁₁H₁₈N₂O₂

[ Molecular Weight ]:
210.27

[ Flash Point ]:
212.4±25.7 °C

[ Exact Mass ]:
210.136826

[ PSA ]:
49.41000

[ LogP ]:
-0.84

[ Vapour Pressure ]:
0.0±1.0 mmHg at 25°C

[ Index of Refraction ]:
1.530

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: UY8708800

CHEMICAL NAME :: Pyrrolo(1,2-a)pyrazine-1,4-dione, hexahydro-3-isobutyl-, stereoisomer

CAS REGISTRY NUMBER :: 2873-36-1

BEILSTEIN REFERENCE NO. :: 0085716

LAST UPDATED :: 199612

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C11-H18-N2-O2

MOLECULAR WEIGHT :: 210.31

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 80 mg/kg

TOXIC EFFECTS :: Tumorigenic - facilitates action of known carcinogen

REFERENCE :: 85ERAY "Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978 Volume(issue)/page/year: 2,1354,1978

Safety Information

[ HS Code ]:
2933990090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933990090

[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%