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ChemicalBook--->CAS DataBase List--->4549-02-4

4549-02-4

4549-02-4 Structure

4549-02-4 Structure
IdentificationBack Directory
[Name]

MACULOSIN
[CAS]

4549-02-4
[Synonyms]

A-19C
MACULOSIN
ML-1532II
CYCLO(-PRO-TYR)
Antibiotic A-19C
cyclo(L-Pro-L-Tyr)
Cyclo(L-Tyr-L-Pro-)
MACULOSIN USP/EP/BP
Antibiotic ML-1532II
Cyclo(L-prolinyl-L-tyrosine)
(3S,8aS)-Hexahydro-3-[(4-hydroxyphenyl)methyl]pyrrolo[1,2-a]pyrazine-1,4-dione
Pyrrolo[1,2-a]pyrazine-1,4-dione, hexahydro-3-[(4-hydroxyphenyl)methyl]-, (3S,8aS)-
(3S,8aS)-3-(4-hydroxybenzyl)-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-quinone
(3S,8aS)-3-[(4-hydroxyphenyl)methyl]-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione
[Molecular Formula]

C14H16N2O3
[MDL Number]

MFCD03093467
[MOL File]

4549-02-4.mol
[Molecular Weight]

260.29
Chemical PropertiesBack Directory
[Melting point ]

156-159 °C
[Boiling point ]

581.4±43.0 °C(Predicted)
[density ]

1.36±0.1 g/cm3(Predicted)
[storage temp. ]

-15°C
[solubility ]

DMF: soluble; DMSO: soluble; Ethanol: soluble; Methanol: soluble
[form ]

A solid
[pka]

9.92±0.15(Predicted)
[color ]

White to off-white
Safety DataBack Directory
[Symbol(GHS) ]


GHS08,GHS06
[Signal word ]

Danger
[Hazard statements ]

H301-H311-H331-H371
[Precautionary statements ]

P280-P302+P352-P312-P322-P361-P363-P405-P501-P260-P264-P270-P309+P311-P405-P501-P264-P270-P301+P310-P321-P330-P405-P501-P261-P271-P304+P340-P311-P321-P403+P233-P405-P501
Hazard InformationBack Directory
[Description]

Maculosin is a diketopiperazine metabolite produced by A. alternata, L. capsici, Streptomyces, and the Gram-negative, nonobligate predator bacterial strain 679-2. It acts as a host-specific phytotoxin, inducing formation of weeping necrotic lesions in leaves of spotted knapweed (C. maculosa) when used at a concentration of 10 μM. Maculosin reduces the growth of the plant pathogenic bacteria X. axonopodis and R. solanacearum (MICs = 31.25 μg/ml) as well as the pathogenic oomycetes P. cactorum, P. capsici, P. cinnamomi, P. infestans, and P. ultimum when used at concentrations ranging from 10 to 100 mg/ml. Maculosin also inhibits the growth of M. luteus, M. smegmatis, S. cerevisiae, C. albicans, C. neoformans, and A. niger when used in combination with pyrrolnitrin or banegasin.
[Uses]

Cyclo(L-prolinyl-L-tyrosine) is a diketopiperazine derivative isolated from Bacillus thuringiensis and Bacillus endophyticus.
[Uses]

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. 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. Cyclo(L-Pro-L-Tyr) was identified as a host-specific toxin produced by Alternaria alternata on spotted knapweed.
[Definition]

ChEBI: A homodetic cyclic peptide that is a dipeptide composed of L-proline and L-tyrosine joined by peptide linkages.
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