Cyclo(L-Phe-L-Pro)

Base Information

• Chemical Name: Cyclo(L-Phe-L-Pro)
• CAS No.: 3705-26-8
• Molecular Formula: C₁₄H₁₆N₂O₂
• Molecular Weight: 244.293
• European Community (EC) Number: 223-047-0
• DSSTox Substance ID: DTXSID101316106
• Nikkaji Number: J86.567B
• Wikidata: Q27104973
• Metabolomics Workbench ID: 141140
• ChEMBL ID: CHEMBL512845
• Mol file: 3705-26-8.mol

Synonyms:cyclo(L-Phe-L-Pro);cyclo(Phe-Pro);cyclo(phenylalanyl-prolyl)

Chemical Property of Cyclo(L-Phe-L-Pro)

Chemical Property:

• Vapor Pressure: 1.68E-10mmHg at 25°C
• Melting Point: 146-148 °C
• Boiling Point: 509.5°Cat760mmHg
• PKA: 13.21±0.40(Predicted)
• Flash Point: 262°C
• PSA: 49.41000
• Density: 1.26g/cm³
• LogP: 0.98520
• Storage Temp.: -15°C
• Solubility.: Chloroform (Slightly), Ethanol (Slightly, Sonicated)
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 244.121177757
• Heavy Atom Count: 18
• Complexity: 350

Purity/Quality:

99%, ^*data from raw suppliers

Cyclo(L-prolyl-L-phenylalanyl) ^*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=CC=C3
• Isomeric SMILES: C1C[C@H]2C(=O)N[C@H](C(=O)N2C1)CC3=CC=CC=C3
• Uses: Cyclo(L-prolyl-L-phenylalanyl) is a diketopiperazine derivative isolated from Bacillus thuringiensis and Bacillus endophyticus. Cyclo(L-Phe-L-Pro) is a diketopiperazine formed by the fusion of phenylalanine and proline, reported as a secondary metabolite of fungi and bacteria. In Pseudomonas aeruginosa, cyclo(L-Phe-L-Pro) is capable of activating N-acylhomoserine lactones (AHLs). Cyclo(L-Phe-L-Pro) is also capable of activating or antagonizing other LuxR-based quorum-sensing systems. While the mode of action of cyclo(L-Phe-L-Pro) is not known, its activity suggests the existence of cross talk among bacterial signalling systems.

Technology Process of Cyclo(L-Phe-L-Pro)

There total 60 articles about Cyclo(L-Phe-L-Pro) 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: 93.0%

L-phenylalaninyl-L-proline methyl ester hydrochloride (77100-17-5) → (3S,8aS)-3-benzyloctahydropyrrolo[1,2-a]pyrazine-1,4-dione (5654-85-3,14705-60-3,26488-24-4,32021-26-4,43041-16-3,43041-30-1,3705-26-8)

Guidance literature:

With water; triethylamine; at 140 ℃; for 0.166667h; microwave irradiation;

DOI:10.1016/j.tet.2006.05.010

Reference yield: 88.0%

t-butyloxycarbonyl-L-phenylalanyl-L-proline methyl ester (38017-89-9) → (3S,8aS)-3-benzyloctahydropyrrolo[1,2-a]pyrazine-1,4-dione (5654-85-3,14705-60-3,26488-24-4,32021-26-4,43041-16-3,43041-30-1,3705-26-8)

Guidance literature:

In 1,4-dioxane; water; at 130 ℃; for 4h;

DOI:10.1016/j.tetlet.2009.12.134

Reference yield: 82.0%

1-(tert-butoxycarbonyl)-L-proline (15761-39-4,59433-50-0) + N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) → (3S,8aS)-3-benzyloctahydropyrrolo[1,2-a]pyrazine-1,4-dione (5654-85-3,14705-60-3,26488-24-4,32021-26-4,43041-16-3,43041-30-1,3705-26-8)

Guidance literature:

Multistep reaction;

DOI:10.1016/S0040-4039(01)02005-6

upstream raw materials:

Z-DL-Phe-OH

acetone

1-(3,4,5-tris(octadecyloxy)benzyl)-2,3,4,6,7,8-hexahydro-1H-pyrimido[1,2-a]pyrimidine

(1S)-methyl 2-[(S)-2-amino-3-phenylpropanoyl]cyclopentanecarboxylate

Downstream raw materials:

[(S)-2-((S)-3-Benzyl-1,4-dioxo-hexahydro-pyrrolo[1,2-a]pyrazin-2-yl)-1-benzyloxymethyl-2-oxo-ethyl]-carbamic acid tert-butyl ester

L-Phenylalanyl-D-prolin-lactam

[(S)-1-((3S,8aS)-3-Benzyl-1,4-dioxo-hexahydro-pyrrolo[1,2-a]pyrazine-2-carbonyl)-2-methyl-propyl]-carbamic acid benzyl ester

N--Phe-Pro-Lactam

Refernces

• 1、 Ishizu, Takashi,Tokunaga, Miku,Fukuda, Moeka,Matsumoto, Mana,Goromaru, Takeshi,Takemoto, Soushi. "Molecular capture and conformational change of diketopiperazines containing proline residues by epigallocatechin-3-O-gallate in water". . p. 585 - 589. Retrieved 2021/06/06.
• 2、 Gaidukevich,Rudenkova,Popova,Nikolaevich,Knizhnikov. "Synthesis of 3-Benzylhexahydropyrrolo[1,2-a]pyrazine-1,4-dione". . p. 1562 - 1564. Retrieved 2019/01/04.