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MACULOSIN

MACULOSIN Structure
CAS No.
4549-02-4
Chemical Name:
MACULOSIN
Synonyms
A-19C;0/4/49;ML-1532II;MACULOSIN;Maculosin TFA;CYCLO(-PRO-TYR);Antibiotic A-19C;cyclo(L-Pro-L-Tyr);Cyclo(L-Tyr-L-Pro-);MACULOSIN USP/EP/BP
CBNumber:
CB0265753
Molecular Formula:
C14H16N2O3
Molecular Weight:
260.29
MOL File:
4549-02-4.mol
MSDS File:
SDS
Modify Date:
2024/7/2 8:54:57

MACULOSIN 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 Chemical Properties,Uses,Production

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-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.

MACULOSIN Preparation Products And Raw materials

Raw materials

Preparation Products

Global( 43)Suppliers
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Dideu Industries Group Limited +86-29-89586680 +86-15129568250 China 25298 58 Inquiry
BOC Sciences 16314854226; +16314854226 United States 19743 58 Inquiry
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DONBOO AMINO ACID COMPANY +8613063595538 China 9365 58 Inquiry
Shaanxi Xinyan Bomei Biotechnology Co., Ltd. 029-86217788 13892832556 China 1992 58 Inquiry
United States Biological 800.520.3011 or 781.639.5092 United States 6256 80 Inquiry
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 (3S,8aS)-3-[(4-hydroxyphenyl)methyl]-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione cyclo(L-Pro-L-Tyr) (3S,8aS)-Hexahydro-3-[(4-hydroxyphenyl)methyl]pyrrolo[1,2-a]pyrazine-1,4-dione Cyclo(L-prolinyl-L-tyrosine) Pyrrolo[1,2-a]pyrazine-1,4-dione, hexahydro-3-[(4-hydroxyphenyl)methyl]-, (3S,8aS)- MACULOSIN USP/EP/BP cyclo(L-Pro-L-Tyr),Maculosin inhibit,Cyclo(Tyr-Pro),Alternaria alternata,anti-cancer,liver cancer,non-toxicity,967564,Inhibitor,cyclo(L Pro L Tyr),antioxidant,spotted knapweed,cyclo(LProLTyr),Maculosin 0/4/49 Maculosin TFA 4549-02-4 Cell Signaling and Neuroscience Cell Biology BioChemical Gene Regulation and Expression Reagents Tools for Gene Regulation Research