4549-02-4

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 NO: 4549-02-4
• Molecular Formula: C₁₄H₁₆N₂O₃
• Molecular Weight: 260.29
• Mol File: 4549-02-4.mol
• Article Data: 8

Chemical Properties

• Melting Point: 156-159 °C
• Boiling Point: 581.4°Cat760mmHg
• Flash Point: 305.4°C
• Appearance: /
• Density: 1.36g/cm³
• Vapor Pressure: 4.07E-14mmHg at 25°C
• Refractive Index: 1.644
• Storage Temp.: -15°C
• PKA: 9.92±0.15(Predicted)
• CAS DataBase Reference: MACULOSIN(CAS DataBase Reference)
• NIST Chemistry Reference: MACULOSIN(4549-02-4)
• EPA Substance Registry System: MACULOSIN(4549-02-4)

Safety Data

• Hazardous Substances Data: 4549-02-4(Hazardous Substances Data)

Usage

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

Different sources of media describe the Uses of 4549-02-4 differently. You can refer to the following data:
1. Cyclo(L-prolinyl-L-tyrosine) is a diketopiperazine derivative isolated from Bacillus thuringiensis and Bacillus endophyticus.
2. 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.

InChI:InChI=1/C14H16N2O3/c17-10-5-3-9(4-6-10)8-11-14(19)16-7-1-2-12(16)13(18)15-11/h3-6,11-12,17H,1-2,7-8H2,(H,15,18)/t11-,12-/m0/s1

Upstream product

• 82609-80-1 methyl 1-(2-((t-butoxycarbonyl)amino)-3-(4-hydroxyphenyl)propanoyl)pyrrolidine-2-carboxylate 
• 41324-66-7 H-Pro-OBzl 
• 85676-37-5 Boc-Tyr-Pro-OBzl 
• 7531-52-4 L-prolinamide 
• 3978-80-1 Boc-Tyr-OH 
• 74201-47-1 (tert-butoxycarbonyl)-L-tyrosyl-L-proline 

Downstream Products

• 1227828-31-0 4-(((3S,8aS)-1,4-dioxooctahydropyrrolo[1,2-a]pyrazin-3-yl)methyl)phenyl trifluoromethanesulfonate 
• 61117-56-4 (3S,8aR)-3-(4-hydroxybenzyl)hexahydropyrrolo[1,2-a]pyrazine-1,4-dione 
• 60-18-4 L-tyrosine 
• 147-85-3 L-proline 
• 1589529-08-7 (3S,8aS)-3-(4-allylbenzyl)hexahydropyrrolo[1,2-a]pyrazine-1,4-dione 

Relevant articles and documents

Molecular capture and conformational change of diketopiperazines containing proline residues by epigallocatechin-3-O-gallate in water

The addition of an aqueous solution of diketopiperazine cyclo(Pro-Xxx) (Xxx: amino acid residue) to an aqueous solution of (?)-epigallocatechin-3-O-gallate (EGCg) led to precipitation of the complex of EGCg and cyclo(Pro-Xxx). The molecular capture abilities of cyclo(Pro-Xxx) using EGCg were evaluated by the ratio of the amount of cyclo(Pro-Xxx) included in the precipitates of the complex with EGCg to that of the total cyclo(Pro-Xxx) used. Stronger hydrophobicity of the side chain of the amino acid residue of cyclo(Pro-Xxx) led to a higher molecular capture ability. Furthermore, the molecular capture ability decreased when the side chain of the amino acid residue had a hydrophilic hydroxyl group. When diketopiperazine cyclo(Pro-Xxx), excluding cyclo(D-Pro-L-Ala), was taken into the hydrophobic space formed by the three aromatic A, B, and B′ rings of EGCg, and formed a complex, their conformation was maintained in the hydrophobic space. Based on nuclear Overhauser effect (NOE) measurement, the 3-position methyl group of cyclo(D-Pro-L-Ala) in D2O was axial, whereas that of cyclo(L-Pro-L-Ala) was equatorial. When cyclo(D-Pro-L-Ala) was taken into the hydrophobic space of EGCg and formed a 2:2 complex, its 3-position methyl group changed from the axial position to the equatorial position due to steric hindrance by EGCg.

Crystal structure and spectroscopic properties of cyclic dipeptide: A racemic mixture of cyclo(D-Prolyl-L-Tyrosyl) and cyclo(L-Prolyl-D-Tyrosyl)

Two diastereoisomers of cyclo(Pro-Tyr) have been synthesized simultaneously. The crystal structures and conformations of both cyclo(L-Pro-L-Tyr) and a racemic mixture of cyclo(D-Pro-L-Tyr) and cyclo(L-Pro-DTyr), abbreviated as rac-cyclo(D-Pro-L-Tyr/L-Pro-D-Tyr), have been determined by a single-crystal X-ray diffraction study at low temperature. The crystals of rac-cyclo(D-Pro-L-Tyr/L-Pro-D-Tyr) belong to orthorhombic space group Pna21 with a = 10.755 (1), b = 12.699 (1), c = 9.600 (1) A and Z = 4. The tyrosine side chain is folded towards the diketopiperazine (DKP) ring. The DKP ring adopts a twist boat conformation with pseudo symmetry C2v. The pyrrolidine ring has an envelope conformation with the N5, C4, C7 and C8 atoms in a plane. The crystal of rac-cyclo(D-Pro-L-Tyr/L-Pro-D-Tyr) is stabilized by hydrogen bonds between amide N2-H2 and carbonyl oxygen O2 in the neighbor. The hydroxyl group of tyrosine residue is also hydrogen bonded to the oxygen of the carbonyl group of the DKP ring in the next molecule. The spectroscopic properties of both isomers are also described.

An efficient green synthesis of proline-based cyclic dipeptides under water-mediated catalyst-free conditions

l-Proline-based cyclic dipeptides were synthesized from N-Boc-protected dipeptide methyl esters under catalyst-free condition using water as a solvent. One-pot deprotection and cyclization have been used as the key steps, providing an efficient and environmentally friendly approach. Clean reaction conditions, easy isolation, and good yields of cyclic dipeptides are the salient features of the proposed methodology.