15180-22-0

Basic information

• Product Name: (2S,5S)-2-Benzyl-5-methylpiperazine-3,6-dione
• Synonyms: (2S,5S)-2-Benzyl-5-methylpiperazine-3,6-dione;(3S,6S)-3-Benzyl-6-methyl-2,5-piperazinedione
• CAS NO: 15180-22-0
• Molecular Formula: C₁₂H₁₄N₂O₂
• Molecular Weight: 218.25
• Mol File: 15180-22-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (2S,5S)-2-Benzyl-5-methylpiperazine-3,6-dione(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,5S)-2-Benzyl-5-methylpiperazine-3,6-dione(15180-22-0)
• EPA Substance Registry System: (2S,5S)-2-Benzyl-5-methylpiperazine-3,6-dione(15180-22-0)

Safety Data

• Hazardous Substances Data: 15180-22-0(Hazardous Substances Data)

Upstream product

• 35661-39-3 N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine 
• 35661-40-6 N-Fmoc L-Phe 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 1416817-74-7 C₁₄H₁₇N₃O₃ 
• 1115-59-9 (S)-alanine ethyl ester hydrochloride 
• 15761-38-3 L-N-Boc-Ala 
• 15136-29-5 (S)-methyl 2-((S)-2-((tert-butoxycarbonyl)amino)-3-phenylpropanamido)propanoate 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 2280-66-2 N-tert-butyloxycarbonylalanylphenylalanine methyl ester 
• 2577-90-4 methyl (2S)-2-amino-3-phenylpropanoate 
• 3235-14-1 (S)-2-((S)-2-Benzyloxycarbonylamino-propionylamino)-3-phenyl-propionic acid methyl ester 
• 40298-89-3 L-alanyl-L-phenylalanine methyl ester 
• 150582-57-3 (S)-4-methyl-2,2-bis-trifluoromethyl-oxazolidin-5-one 

Downstream Products

• 17585-69-2 L-phenylalanine hydrochloride 
• 6003-05-0 L-alanine hydrochloride 

Relevant articles and documents

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.

Interfacial supramolecular biomimetic epoxidation catalysed by cyclic dipeptides

We synthesised a library of cis- and trans-cyclic dipeptides and evaluated their efficacy as catalysts in the asymmetric Weitz-Scheffer epoxidation of trans-chalcone. A thorough investigation relying on structure-activity studies and computational studies provided insights into the mechanism of the process. Our results revealed some structural features required for efficient conversion and for introduction of chirality into the product. The cyclic dipeptide acts as a catalyst by templating a supramolecular arrangement at the aqueous-organic interface required for efficient transformations to occur. Among all cyclic dipeptides investigated, cyclo(Leu-Leu) was the most efficient supramolecular catalyst.

Synthesis and conformational characterization of diketopiperazines bearing a benzyl moiety

Diketopiperazines bearing a benzyl moiety with different para-substituents were synthesized and analyzed by 1HNMR spectroscopy. All of these diketopiperazines were found to adopt a folded conformation according to the upfield chemical shift of the cis-proton (cis to the benzyl moiety) due to a shielding effect in the 1HNMR spectra. An intramolecular CH-π interaction appears to be an important factor for the folded conformation due to the effects of para-substituents on the benzyl group.

Facile one-step synthesis of 2,5-diketopiperazines

We report a one-step protocol for the general synthesis of 2,5-diketopiperazines from an Fmoc-protected amino acid and an amino acid ester. The application of the method is highlighted by rapid and efficient preparation of various 2,5-diketopiperazines.

Dibutylphosphate (DBP) mediated synthesis of cyclic N,N′- disubstituted urea derivatives from amino esters: A comparative study

The N,N′-disubstituted urea derivatives such as amino acid hydantoins and dihydrouracil derivatives were prepared starting from natural and unnatural amino acid esters using dibutylphosphate (DBP). During the attempted synthesis of N-heterocycles with larger than six-membered rings containing the N,N′-disubstituted urea functionalities, three unexpected products namely squamolone, N-methyl pyrrolidine-2-one, and diketopiperazine were isolated.

Catalytic asymmetric synthesis of substituted morpholines and piperazines

Under two conditions: Hydroamination catalyzed by group 4 metals is featured in the modular and enantioselective synthesis of 3-substituted morpholines and the diastereoselective synthesis of 2,5-substituted piperazines. Copyright

Structures, sensory activity, and dose/response functions of 2,5-diketopiperazines in roasted cocoa nibs (Theobroma cacao)

The taste compounds inducing the blood-like, metallic bitter taste sensation reported recently for a dichloromethane extract prepared from roasted cocoa nibs were identified as a series of 25 diketopiperazines by means of HPLC degustation, LC-MS/MS, and i

Preparation of novel 2-(trialkylsilyl)ethyl linkers and first synthesis of Tryprostatin B on solid phase

Two synthetic methods for novel polymer-supported 2-(trialkylsilyl)ethanol linkers 3 are described. The new silyl linker has been examined as a C-terminal linkage to provide several diketopiperazines. Using this synthetic method, the first solid phase synthesis of Tryprostatin B was accomplished. Several functionalized 2-(trialkylsilyl)ethyl linkers 12-17 are synthesized from 2-(trialkylsilyl)ethanol linkers. During the course of preparations, the new silyl linkers proved resistant to various reaction conditions such as basic and moderately acidic media, oxidation, and elevated thermal conditions.

Conformational effects in reversed-phase liquid chromatographic separation of diastereomers of cyclic dipeptides

The capacity factors, k′, of 11 cyclic dipeptides (X-Y) including diastereomers have been determined on an RP-HPLC column in 30% and 50% methanol and 10%, 30%, and 50% acetonitrile solutions. These factors are roughly correlated with hydrophobic parameters, such as octanol-water partition coefficients estimated and k′ values for alcohols. For a pair of diastereomers of cyclic (L-X-L-Phe) and (L-X-D-Phe) derivatives k′LL is larger than k′LD and for cyclic (D-Ala-L-Trp) and (L-Ala-L-Trp) k′LL is smaller than k′DL, particularly in highly aqueous solutions. These elution orders can be well predicted by the holistic molecular surface area approach which takes into account the folded structures of cyclic dipeptides. The present results will be useful for prediction of the log k′ values of larger peptides and the hydrophobicity and related properties of peptides.

Hexafluoroacetone as Protecting Group and Activating Reagent in Amino Acid and Peptide Chemistry, XI. A New Simple Preparative Access to 2,5-Dioxopiperazines and 2,5-Dioxomorpholines

2,5-Dioxopiperazines with symmetrical as well as unsymmetrical substituent pattern can be obtained via 2,2-bis(trifluoromethyl)-1,3-oxazolidin-5-ones, and 2,5-dioxomorpholines via 2,2-bis(trifluoromethyl)-1,3-dioxolan-4-ones, respectively. Keywords: Hexafluoroacetone; α-Amino acids; α-Hydroxy acids; 2,2-Bis(trifluoromethyl)-1,3-oxazolidin-5-ones; 2,2-Bis(trifluoromethyl)-1,3-dioxolan-4-ones; 2,5-Dioxopiperazines; 2,5-Dioxomorpholines.