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

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

Uses

Used in Plant Pathogen Control:
Maculosin is used as a biocontrol agent for reducing the growth of plant pathogenic bacteria such as X. axonopodis and R. solanacearum, as well as pathogenic oomycetes like P. cactorum, P. capsici, P. cinnamomi, P. infestans, and P. ultimum. It is effective at concentrations ranging from 10 to 100 mg/ml.
Used in Fungal Inhibition:
Maculosin is used as an antifungal agent to inhibit the growth of various fungi, including M. luteus, M. smegmatis, S. cerevisiae, C. albicans, C. neoformans, and A. niger, particularly when used in combination with pyrrolnitrin or banegasin.
Used in Quorum Sensing Regulation:
Maculosin, specifically cyclo(L-Pro-L-Tyr), is used as a modulator of quorum sensing systems in bacteria, such as Pseudomonas aeruginosa. It can activate or antagonize LuxR-based quorum-sensing systems, indicating the presence of cross talk among bacterial signaling systems.
Used in Host-Specific Toxin Production:
Maculosin is used as a host-specific toxin produced by Alternaria alternata on spotted knapweed (C. maculosa), inducing the formation of weeping necrotic lesions in leaves when used at a concentration of 10 μM.

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

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

Downstream Products

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

Diketopiperazines derivatives isolated from Bacillus thuringiensis and Bacillus endophyticus, establishment of their configuration by X-ray and their synthesis

Four known diketopiperazines have been isolated from Bacillus thuringiensis strain and two of them were isolated from Bacillus endophyticus also. Their structure was elucidated by a complete spectroscopy and the configuration of three of them was establis

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.

AGRICULTURAL CHEMICAL CONTAINING 2,5-DIKETOPIPERAZINE DERIVATIVE AS ACTIVE INGREDIENT

Disclosed herein is an agricultural agent containing a 2,5-diketopiperazine derivative capable of controlling plant diseases and promoting plant growth or an agriculturally acceptable salt thereof as an active ingredient.

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.

Novel ester-linked carbohydrate-peptide adducts: Effect of the peptide substituent on the pathways of intramolecular reactions

Carbohydrate-peptide conjugates in which D-glucose is linked through an ester linkage to the carboxy group of Tyr-Pro (2), Tyr-Pro-Phe (5) or Tyr-Pro-Phe-Val (11), through the C6 hydroxy group of the sugar moiety were synthesized to examine the utility of this type of monosaccharide modification for peptide prodrugs. Evidence is provided that glycoconjugates 2, 5, and 11 easily undergo intramolecular chemical transformations, subsequent to attack of the free N-terminal amino group at the peptide backbone or at the anomeric position of the D-glucose moiety, resulting in the formation of diketopiperazine 12, glycosylamine 13, or ketosugar derivative 15. The data indicated that the length and structure of the peptide chain are the main factors that control the intramolecular reactions of the carbohydrate-peptide esters studied.

Cyclodipeptides: Structure and conformation of cyclo(tyrosyl-prolyl)

The structure and conformation of the cyclodipeptide, cyclo(Tyrosyl-Prolyl), cyclo(Tyr-Pro) have been investigated with X-ray crystallographic and spectroscopic methods.Two conformations of cyclo(Tyr-Pro) crystallized in the space group P212su

Studies on analgesic oligopeptides. II. Structure-activity relationship among thirty analogs of a cyclic dipeptide, cyclo(-Tyr-Arg-)

Thirty diketopiperazines were synthesized as analogs of cyclo(-Tyr-Arg-). The analgesic activities of these analogs were evaluated after intracerebral administration in mice. In the cyclo(-X-Arg-) series of analogs, cyclo[-Tyr(Et)-Arg-] showed the most po