19943-16-9

Basic information

• Product Name: CYCLO(-VAL-VAL)
• Synonyms: VAL-VAL DIKETOPIPERAZINE;CYCLO(-VAL-VAL);CYCLO(L-VAL-L-VAL);(3S,6S)-3,6-Bis(1-methylethyl)-2,5-piperazinedione;Cyclo(L-valyl-L-valyl);(3S,6S)-3,6-Diisopropylpiperazine-2,5-dione;Cyclo(L-Val-L-Val)≥ 98% (NMR)
• CAS NO: 19943-16-9
• Molecular Formula: C₁₀H₁₈N₂O₂
• Molecular Weight: 202.29
• Mol File: 19943-16-9.mol

Chemical Properties

• Melting Point: 268℃ (DEC.)
• Boiling Point: 428.7°C at 760 mmHg
• Flash Point: 184.8°C
• Appearance: /
• Density: 1.012
• Vapor Pressure: 1.49E-07mmHg at 25°C
• Refractive Index: 1.455
• Storage Temp.: -15°C
• Solubility: Acetic Acid (Slightly), DMSO (Slightly), Hexane (Slightly)
• PKA: 12.78±0.60(Predicted)
• CAS DataBase Reference: CYCLO(-VAL-VAL)(CAS DataBase Reference)
• NIST Chemistry Reference: CYCLO(-VAL-VAL)(19943-16-9)
• EPA Substance Registry System: CYCLO(-VAL-VAL)(19943-16-9)

Safety Data

• Hazardous Substances Data: 19943-16-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
CYCLO(-VAL-VAL) is used as a research compound for studying the thermodynamics of protein unfolding. Its cyclic structure and dipeptide composition allow scientists to investigate the stability and folding mechanisms of proteins, which is crucial for understanding protein function and developing new drugs targeting specific proteins.
Used in Chemical Research:
CYCLO(-VAL-VAL) serves as a valuable compound in chemical research, particularly in the synthesis of more complex peptides and the study of peptide-protein interactions. Its cyclic nature and simple structure make it an ideal starting point for exploring the properties and potential applications of cyclic peptides in various fields.
Used in Material Science:
The unique properties of CYCLO(-VAL-VAL) also make it a candidate for use in material science, where it could potentially be employed in the development of novel materials with specific properties, such as improved stability or biocompatibility.

InChI:InChI=1/C10H18N2O2/c1-5(2)7-9(13)12-8(6(3)4)10(14)11-7/h5-8H,1-4H3,(H,11,14)(H,12,13)/t7-,8-/m0/s1

Upstream product

• 67-56-1 methanol 
• 3918-93-2 valyl-valine 
• 516-06-3 D,L-valine 
• 13893-45-3 valine ethyl ester 
• 879553-77-2 optically inactive N-(N-benzyloxycarbonyl-valyl)-valine 
• 4070-48-8 L-valine methyl ester 
• 4070-48-8 L-Valine methyl ester 
• 3918-94-3 Val-Val 
• 1999-88-8 methyl (S)-2-((S)-2-benzyloxycarbonyl-amino-3-methylbutyrylamino)-3-methylbutyrate 
• 21761-30-8 L-valyl-L-valine methyl ester 
• 77443-49-3 (S)-benzyl 2-((S)-2-((tert-butoxycarbonyl)amino)-3-methylbutanamido)-3-methylbutanoate 
• 72-18-4 L-valine 
• 6306-52-1 L-valine methylester hydrochloride 
• 640-68-6 D-Val-OH 

Downstream Products

• 154559-11-2 2,5-diisopropylpiperazine 
• 114409-86-8 (2S,5S)-2,5-diisopropyl-1,4-bis(3-phenylpropanoyl)piperazine 
• 2026-48-4 (S)-valinol 
• 114420-47-2 (2S,5S)-1,4-dibenzyl-2,5-diisopropylpiperazine 
• 114409-91-5 (2S,5S)-2,5-bis(isopropyl)piperazine 
• 114362-40-2 (3S,6S)-1,4-dibenzyl-3,6-diisopropyl-piperazine-2,5-dione 

Relevant articles and documents

The Preparation and Resolution of Novel Axially Chiral Pyrazine-Containing P,N Ligands for Asymmetric Catalysis and Their Application in Palladium-Catalysed Allylic Substitution

The design and synthesis of two novel pyrazine-containing ligands, 3,6-diisopropyl-Pyrazinap and Np?Cy-Pyrazinap, has been described. Their synthesis was accomplished in six and nine steps, respectively, in which the key steps were the formation of the biaryl linkage through a Suzuki cross-coupling reaction and the formation of the aryl to phosphorus bond employing nickel catalysis. Both ligands were resolved through the formation of diastereomeric palladacycles and in the case of the isolated diastereomer formed from 3,6-diisopropyl-Pyrazinap, an X-ray crystal structure showed the axial chirality to possess (S)-configuration. The two enantiopure ligands were applied to the palladium-catalysed allylic alkylation of 1,3-diphenylprop-2-enyl acetate with dimethyl malonate and afforded conversions of up to 100 % and 99 % with enantioselectivities of up to 92 % ee and 78 % ee, respectively. A series of 1,1,3-triphenylallyl and 1,3-diphenylallyl palladium complexes were prepared and their solution structures and dynamic behaviour elucidated by 2D-COSY and NOESY NMR spectroscopic experiments.

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.

CHIRAL FLUORINATING REAGENTS

This invention relates to fluorinating agents and, more particularly, to chiral non-racemic fluorinating agents useful for enantioselective fluorination, as well as to their synthesis and use and other subject matter. The fluorinating agents are based on a substituted 1,4-diazabicyclo[2.2.2]octane (DABCO) skeleton and provide electrophillic fluorine enantioselectively.

Linear and cyclic dipeptides with antimalarial activity

Several natural and synthetic polypeptides possess important antimalarial activity. Shorter peptides with potent antimalarial activity have also been described, among them linear di-, tri-, tetra- and pentapeptides and their cyclic analogs. In an attempt

Synthesis of peptides and pyrazines from β-amino alcohols through extrusion of h2 catalyzed by ruthenium pincer complexes: Ligand-controlled selectivity

Your choice: The choice of the Ru-pincer-complex catalyst determines if peptides or pyrazines are formed from β-amino alcohols. Use of PNN complex 1 leads to linear poly(alanine) or to cyclic dipeptides, depending on the R group (see scheme). With the PNP

Cyclic dipeptides: Catalyst/promoter-free, rapid and environmentally benign cyclization of free amino acids

"The best catalyst is no catalyst." With growing public concern over global warming and the amount of greenhouse gases, it is important to reduce the amount of chemicals and eliminate waste, to obtain better results in a simple, selective, safe, and environmentally benign fashion compared to conventional tedious chemical synthesis. Herein, we disclose an environmentally benign, rapid, catalyst/promoter/coupling reagent-free cyclization procedure of free amino acids to furnish exclusively cyclic dipeptides (2,5- diketopiperazines, DKPs) in excellent or even quantitative yield, along with their solid state self-assembling properties. This process is extremely simple and highly efficient with little or no traditional synthetic skills and without any chromatographic purification. Synthesis of structurally diverse DKPs has been achieved with a dramatic decrease in the reaction time, the amount/number of solvents used, a significant increase in the yield and nearly complete elimination of waste. As a result, this is an excellent example for the environmentally benign, clean and green chemistry concept. The most exciting outcome of our investigation is an unusual case of chiral self-recognition encountered upon the cyclization of rac-pipecolic acid, which resulted in the formation of the meso-product exclusively.

Investigation of reaction mechanism of amino acids and phosphorus trichloride by 31P NMR and ESI-MS/MS

The reaction of amino acids and phosphorus trichloride in THF was studied by 31P NMR tracing and ESI-MS/MS. A series of hydridophoranes and cyclic dipeptides were obtained. The reaction presented interesting diversity and the reaction mechanism was proposed. The mechanism suggests that phosphorus plays an important role in the synthesis of amino acid hydridophorane and cyclic dipeptides. The results also show that 31P NMR and ESI-MS/MS are useful tools for the investigation of reaction mechanism. Copyright

Chiral eighteen-component three-dimensional supramolecular entities stabilized by the hydrogen bonding and coordination interactions

A new class of chiral eighteen-component three-dimensional supramolecular entities has been assembled in toluene and chloroform from twelve zinc porphyrin-appended 2-(ethylamino)- pyrimido[4,5-b][1,8]naphthyridin-4(3H)-one monomers and six chiral bipyridy

Fragmentation of deprotonated cyclic dipeptides by electrospray ionization mass spectrometry

The fragmentation pathways of deprotonated cyclic dipeptides have been studied by electrospray ionization multi-stage mass spectrometry (ESI-MSn) in negative mode. The results showed that the fragmentation pathways of deprotonated cyclic dipeptides depend