7280-77-5

Basic information

• Product Name: cyclo(leucyl-phenylalanyl)
• Synonyms: cyclo(leucyl-phenylalanyl);(3S,6S)-3-Benzyl-6-isobutyl-2,5-piperazinedione;3-Benzyl-6-isobutyl-2,5-dioxopiperazine;Cyclo(L-leucyl-L-phenylalanyl);L-Phenylalanyl-L-leucine diketopiperazine;cyclo(L-phenylalanyl-L-leucyl);Cyclo(L-Phe-L-Leu)
• CAS NO: 7280-77-5
• Molecular Formula: C₁₅H₂₀N₂O₂
• Molecular Weight: 260.335
• Mol File: 7280-77-5.mol
• Article Data: 14

Chemical Properties

• Melting Point: 282℃ (DEC.)
• Boiling Point: 521°Cat760mmHg
• Flash Point: 205.3°C
• Appearance: /
• Density: 1.081
• Vapor Pressure: 5.89E-11mmHg at 25°C
• Refractive Index: 1.519
• Storage Temp.: Store at 0°C
• CAS DataBase Reference: cyclo(leucyl-phenylalanyl)(CAS DataBase Reference)
• NIST Chemistry Reference: cyclo(leucyl-phenylalanyl)(7280-77-5)
• EPA Substance Registry System: cyclo(leucyl-phenylalanyl)(7280-77-5)

Safety Data

• Hazardous Substances Data: 7280-77-5(Hazardous Substances Data)

Usage

Uses

Cyclo(L-Leu-L-Phe) is also able to cause gelation in a wide variety of organic fluids, including edible oils, glyceryl esters, alcohols, and aromatic molecules.

Definition

ChEBI: A member of the class of 2,5-diketopiperazines that is piperazine-2,5-dione in which one hydrogen at position 3 and one hydrogen at position 6 are replaced by benzyl and isobutyl groups (the 3S,6S-diastereomer).

InChI:InChI=1/C15H20N2O2/c1-10(2)8-12-14(18)17-13(15(19)16-12)9-11-6-4-3-5-7-11/h3-7,10,12-13H,8-9H2,1-2H3,(H,16,19)(H,17,18)

Upstream product

• 60566-42-9 L-phenylalanyl-L-leucine ethyl ester 
• 3303-55-7 L-Phe-Leu 
• 3063-05-6 Leu-Phe-OH 
• 38155-45-2 methyl L-phenylalanyl-L-leucinate hydrochloride 
• 2953-42-6 Z-phenylalanylleucine ethyl ester 
• 13139-15-6 N-tert-butoxycarbonyl-L-leucine 
• 15136-32-0 (N-(tert-butoxycarbonyl)-L-leucinyl)-L-phenylalanine methyl ester 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 3081-24-1 H-Phe-OEt 
• 6461-07-0 methyl (S)-2-[(S)-2-amino-4-methylpentanamido]-3-phenylpropanoate hydrochloride 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 2666-93-5 (S)-Leu-OMe 
• 1416817-77-0 C₁₇H₂₃N₃O₃ 
• 2743-60-4 L-Leucine ethyl ester 

Downstream Products

• 1222-90-8 (3Z,6Z)-3-benzylidene-6-(2-methylpropenyl)piperazine-2,5-dione 
• 74124-69-9 (3Z,6S)-3-benzylidene-6-isobutylpiperazine-2,5-dione 

Relevant articles and documents

Unified enantioselective total synthesis of 3,6-dioxygenated diketopiperazine natural products, diatretol and lepistamides A, B and C

The concise enantioselective total synthesis of Diatretol (1) has been achieved via 9 steps with 30％ yield. The synthetic approach involves stereoselective oxidation and regioselective transacetalization utilizing a folded conformation induced by an intramolecular CH/π interaction. In addition, we have also achieved total synthesis of three diketopiperazine natural products, Lepistamides A (2), B (3) and C (4).

Anti-biofilm and anti-adherence properties of novel cyclic dipeptides against oral pathogens

Microorganisms embedded in a biofilm are significantly more resistant to antimicrobial agents and the defences of the human immune system, than their planktonic counterpart. Consequently, compounds that can inhibit biofilm formation are of great interest for novel therapeutics. In this study, a screening approach was used to identify novel cyclic dipeptides that have anti-biofilm activity against oral pathogens. Five new active compounds were identified that prevent biofilm formation by the cariogenic bacterium Streptococcus mutans and the pathogenic fungus Candida albicans. These compounds also inhibit the adherence of microorganisms to a hydroxylapatite surface. Further investigations were conducted on these compounds to establish the structure–activity relationship, and it was deduced that the common cleft pattern is required for these molecules to act effectively against biofilms.

Marine natural occurring 2,5-diketopiperazines: Isolation, synthesis and optical properties

Seven 2,5-diketopiperazines (DKPs) were isolated from the Fijian marine sponge Acanthella cavernosa. NMR and circular dichroism (CD) comparison with synthetic L-L DKPs allowed us to determine unambiguously the L-L absolute configuration of the natural DKPs. This work initiated the setting up of an optical properties database of natural DKPs, including specific rotation and CD.