3705-26-8

Basic information

• Product Name: CYCLO(-PHE-PRO)
• Synonyms: (3S-trans)-3-benzylhexahydropyrrolo[1,2-a]pyrazine-1,4-dione;(3S,8aS)-3-Benzyl-6,7,8,8aα-tetrahydropyrrolo[1,2-a]pyrazine-1,4(2H,3H)-dione;(3S,8aS)-3β-Benzyl-6,7,8,8a-tetrahydropyrrolo[1,2-a]pyrazine-1,4(2H,3H)-dione;(3S,8aα)-3β-Benzyloctahydropyrrolo[1,2-a]pyrazine-1,4-dione;Cyclo(L-Phe-L-Pro-);Cyclo(Pro-Phe-);(3S)-2,3,6,7,8,8aβ-Hexahydro-3β-(phenylmethyl)pyrrolo[1,2-a]pyrazine-1,4-dione;Cyclo(D-Pro-L-Phe-)
• CAS NO: 3705-26-8
• Molecular Formula: C₁₄H₁₆N₂O₂
• Molecular Weight: 244.29
• EINECS: 223-047-0
• Mol File: 3705-26-8.mol
• Article Data: 29

Chemical Properties

• Melting Point: 146-148 °C
• Boiling Point: 509.5°Cat760mmHg
• Flash Point: 262°C
• Appearance: /
• Density: 1.26g/cm³
• Vapor Pressure: 1.68E-10mmHg at 25°C
• Refractive Index: 1.614
• Storage Temp.: -15°C
• Solubility: Chloroform (Slightly), Ethanol (Slightly, Sonicated)
• PKA: 13.21±0.40(Predicted)
• CAS DataBase Reference: CYCLO(-PHE-PRO)(CAS DataBase Reference)
• NIST Chemistry Reference: CYCLO(-PHE-PRO)(3705-26-8)
• EPA Substance Registry System: CYCLO(-PHE-PRO)(3705-26-8)

Safety Data

• Hazardous Substances Data: 3705-26-8(Hazardous Substances Data)

Usage

Description

CYCLO(-PHE-PRO), also known as Cyclo(L-prolyl-L-phenylalanyl), is a diketopiperazine derivative that has been isolated from Bacillus thuringiensis and Bacillus endophyticus. It is a secondary metabolite of fungi and bacteria, formed by the fusion of phenylalanine and proline. CYCLO(-PHE-PRO) is a white powder and has been reported to have various applications in different industries.

Uses

Used in Bacterial Communication:
CYCLO(-PHE-PRO) is used as a signaling molecule for activating N-acylhomoserine lactones (AHLs) in Pseudomonas aeruginosa. This application is crucial for understanding and potentially manipulating bacterial communication and behavior.
Used in Quorum-Sensing Systems:
CYCLO(-PHE-PRO) is used as an activator or antagonist for LuxR-based quorum-sensing systems. Its ability to interact with these systems suggests the existence of cross talk among bacterial signaling systems, which can be exploited for various biotechnological and medical applications.
Used in Pharmaceutical Industry:
CYCLO(-PHE-PRO) is used as a potential therapeutic agent due to its interactions with bacterial signaling systems. This application is based on the idea that modulating bacterial communication can lead to the development of new treatments for bacterial infections and other related conditions.
Used in Research and Development:
CYCLO(-PHE-PRO) is used as a research tool for studying the mechanisms of bacterial communication and quorum-sensing systems. This application is important for advancing our understanding of bacterial behavior and developing new strategies to combat bacterial infections.
Used in Agricultural Industry:
CYCLO(-PHE-PRO) is used as a bioactive compound in the development of new biopesticides, leveraging its interactions with bacterial signaling systems to control harmful bacteria that affect crop health and yield.

InChI:InChI=1/C14H16N2O2/c17-13-12-7-4-8-16(12)14(18)11(15-13)9-10-5-2-1-3-6-10/h1-3,5-6,11-12H,4,7-9H2,(H,15,17)/t11-,12-/m0/s1

Upstream product

• 3588-57-6 Z-DL-Phe-OH 
• 67-64-1 acetone 
• 955095-22-4 1-(3,4,5-tris(octadecyloxy)benzyl)-2,3,4,6,7,8-hexahydro-1H-pyrimido[1,2-a]pyrimidine 
• 69936-03-4 (1S)-methyl 2-[(S)-2-amino-3-phenylpropanoyl]cyclopentanecarboxylate 
• 35446-32-3 (S)-3-((Ξ)-benzylidene)-hexahydro-pyrrolo[1,2-a]pyrazine-1,4-dione 
• 100665-27-8 (5S,6aR,10bR,10cS)-5-Benzyl-10b-hydroxy-hexahydro-8-thia-3a,5a,10a-triaza-cyclopenta[c]fluorene-4,6,10-trione 
• 57177-79-4 (S)-tert-butyl 2-(((S)-1-methoxy-1-oxo-3-phenylpropan-2-yl)carbamoyl)pyrrolidine-1-carboxylate 
• 214849-88-4 (S)-3-[(Z)-benzylidene]hexahydropyrrolo[1,2-a]pyrazine-1,4-dione 
• 87900-97-8 N-(N-phenylacetyl-Ala)-cyclo-(Phe-Pro) 
• 54793-80-5 (S)-proline-(S)-phenylalanine methyl ester 
• 13589-02-1 L-prolyl-L-phenylalanine 
• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 

Downstream Products

• 3919-02-6 N-L-prolyl-L-phenylalanine 
• 78452-06-9 [(S)-1-((3S,8aS)-3-Benzyl-1,4-dioxo-hexahydro-pyrrolo[1,2-a]pyrazine-2-carbonyl)-2-methyl-propyl]-carbamic acid benzyl ester 
• 96625-34-2 N--Phe-Pro-Lactam 
• 50868-53-6 N-(d-Lysergyl-L-valyl)-L-phenylalanyl-L-prolin-lactam 
• 78452-05-8 [(S)-1-((3S,8aS)-3-Benzyl-1,4-dioxo-hexahydro-pyrrolo[1,2-a]pyrazine-2-carbonyl)-2-methyl-propyl]-carbamic acid tert-butyl ester 
• 81531-47-7 N--Phe-Pro-Lactam 
• 914771-44-1 (3S,8aS)-3-benzyloctahydropyrrolo[1,2-a]pyrazine 
• 32021-26-4 3-benzylhexahydropyrrolo[1,2-a]pyrazin-1,4-dione 
• 95713-60-3 L-Phe-L-FDAA 
• 147-85-3 L-proline 
• 95713-61-4 L-FDAA-D-Phe 
• 128425-02-5 L-FDAA-L-Pro 
• 673-06-3 D-(R)-phenylalanine 

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.

Antidiabetic in vitro and in vivo evaluation of cyclodipeptides isolated from Pseudomonas fluorescens IB-MR-66e

Three cyclodipeptides [cyclo(l-Pro-l-Leu), 1; cyclo(l-Pro-l-Val), 2; and cyclo(l-Pro-l-Phe), 3] were isolated from Pseudomonas fluorescens IB-MR-66e. The structures were established by spectral means and corroborated by synthesis. The antidiabetic potential of compounds 1-3 was explored in vivo, in vitro and in silico. The three peptides showed important inhibitory activity against the α-glucosidase enzyme. Further analysis in vivo using a sucrose tolerance test corroborated that compounds 1 and 3 (1-30 mg kg-1) significantly reduced the postprandial state. Peptide 1 (1-30 mg kg-1) also reduced the postprandial peak after a glucose challenge and exhibited significant hypoglycemia during an insulin tolerance test; thus, its antidiabetic action involved also an improvement of insulin utilization not related to Akt phosphorylation nor to an increment in mitochondrial bioenergetics nor insulin secretion.

Evaluation of two cyclic di-peptides as inhibitors of CCL2 induced chemotaxis

Monocyte chemoattractant protein (CCL2) plays a major role in the recruitment of monocytes during inflammation. In this study we analysed properties of synthetic CCL2 inhibitors in inhibiting CCL2 mediated monocyte migration. Using trans-endothelial chemotaxis assays compounds C1 and C5 were found to significantly reduce CCL2 mediated migration. Flow based adhesion assays showed reduction in adhesion to VCAM-1 in the presence of 10 nM CCL2 and 50 μM C5 (p 0.05). Further studies with these compounds can aid in their development as anti-inflammatory therapies. The Royal Society of Chemistry 2013.