Maculosin

Base Information

• Chemical Name: Maculosin
• CAS No.: 4549-02-4
• Molecular Formula: C14H16 N2 O3
• Molecular Weight: 260.293
• Hs Code.: 2933990090
• European Community (EC) Number: 686-487-6
• DSSTox Substance ID: DTXSID30196526
• Nikkaji Number: J92.068A
• Wikidata: Q27089361
• Metabolomics Workbench ID: 68124
• ChEMBL ID: CHEMBL359788
• Mol file: 4549-02-4.mol

Synonyms:cyclo(L-Pro-L-Tyr);maculosin

Chemical Property of Maculosin

Chemical Property:

• Vapor Pressure: 4.07E-14mmHg at 25°C
• Melting Point: 156-159 °C
• Boiling Point: 581.4°Cat760mmHg
• PKA: 9.92±0.15(Predicted)
• Flash Point: 305.4°C
• PSA: 69.64000
• Density: 1.36g/cm³
• LogP: 0.69080
• Storage Temp.: -15°C
• XLogP3: 1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 260.11609238
• Heavy Atom Count: 19
• Complexity: 377

Purity/Quality:

99%+, ^*data from raw suppliers

Cyclo(L-prolinyl-L-tyrosine) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC2C(=O)NC(C(=O)N2C1)CC3=CC=C(C=C3)O
• Isomeric SMILES: C1C[C@H]2C(=O)N[C@H](C(=O)N2C1)CC3=CC=C(C=C3)O
• 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. 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.

Technology Process of Maculosin

There total 13 articles about Maculosin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 84.0%

methyl 1-(2-((t-butoxycarbonyl)amino)-3-(4-hydroxyphenyl)propanoyl)pyrrolidine-2-carboxylate (82609-80-1) → maculosin-1 (4549-02-4)

Guidance literature:

In water; at 130 ℃; for 4h;

DOI:10.1016/j.tetlet.2009.12.134

Reference yield: 78.0%

C19H26N2O6 → maculosin-1 (4549-02-4)

Guidance literature:

C₁₉H₂₆N₂O₆; With hydrogenchloride; In water; ethyl acetate; for 1h;

With sodium hydroxide; In water; ethyl acetate; at 20 ℃; for 0.5h;

DOI:10.1016/j.tetlet.2016.04.117

Reference yield: 77.0%

6-O-(L-tyrosyl-L-prolyl)-D-glucopyranose trifluoroacetate → maculosin-1 (4549-02-4)

Guidance literature:

In pyridine; acetic acid; at 50 ℃; for 24h;

DOI:10.1002/1099-0690(200104)2001:8<1533::aid-ejoc1533>3.0.co;2-y

upstream raw materials:

(tert-butoxycarbonyl)-L-tyrosyl-L-proline

Boc-Tyr-OH

L-prolinamide

Boc-Tyr-Pro-OBzl

Downstream raw materials:

L-tyrosine

L-proline

4-(((3S,8aS)-1,4-dioxooctahydropyrrolo[1,2-a]pyrazin-3-yl)methyl)phenyl trifluoromethanesulfonate

(3S,8aS)-3-(4-allylbenzyl)hexahydropyrrolo[1,2-a]pyrazine-1,4-dione

Refernces

• 1、 Sansinenea, Estibaliz,Salazar, Francisco,Jiménez, Jacqueline,Mendoza, ángel,Ortiz, Aurelio. "Diketopiperazines derivatives isolated from Bacillus thuringiensis and Bacillus endophyticus, establishment of their configuration by X-ray and their synthesis". . p. 2604 - 2607. Retrieved 2016/06/01.
• 2、 -. "AGRICULTURAL CHEMICAL CONTAINING 2,5-DIKETOPIPERAZINE DERIVATIVE AS ACTIVE INGREDIENT". Paragraph 0033. . Retrieved 2013/06/05.