MACULOSIN
MACULOSIN Basic information
- Product Name:
- MACULOSIN
- Synonyms:
-
- MACULOSIN
- CYCLO(-PRO-TYR)
- A-19C
- Antibiotic A-19C
- Antibiotic ML-1532II
- Cyclo(L-Tyr-L-Pro-)
- ML-1532II
- (3S,8aS)-3-(4-hydroxybenzyl)-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-quinone
- CAS:
- 4549-02-4
- MF:
- C14H16N2O3
- MW:
- 260.29
- Mol File:
- 4549-02-4.mol
MACULOSIN Chemical Properties
- 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
MACULOSIN Usage And Synthesis
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.
MACULOSINSupplier
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- 21-61263452 13641803416
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MACULOSIN(4549-02-4)Related Product Information
- CYCLO(-PRO-VAL)
- 1-[[4-[(4-Fluoro-2-methyl-1H-indol-5-yl)oxy]-5-methylpyrrolo[2,1-f][1,2,4]triazin-6-yl]oxy]-2-propanol
- Cyclo(-Phe-Tyr)
- CYCLO(-MET-PRO)
- cyclo(Pro-Ser)
- cyclo(Pro-Asp)
- cyclo(Pro-Glu)
- CYCLO(-PHE-PRO)
- cyclo(Pro-Lys)
- cyclo(Pro-Asn)
- cyclo(Pro-Gln)
- cyclo(Pro-Cys)
- MACULOSIN
- CYCLO(-GLY-PHE)
- (S,S)-3-BENZYL-1,4-DIAZABICYCLO[4.3.0]NONANE
- (3S)-3-((4-HYDROXYPHENYL)METHYL)-2,5-PIPERAZINEDIONE
- (R)-HEXAHYDROPYRROLO[1,2-A]PYRAZIN-1(2H)-ONE
- CYCLO(-GLY-PRO)