952-45-4Relevant academic research and scientific papers
Using fast scanning calorimetry to study solid-state cyclization of dipeptide L-leucyl-L-leucine
Buzyurov, Aleksey V.,Gerasimov, Alexander V.,Gorbatchuk, Valery V.,Safiullina, Aisylu S.,Schick, Christoph,Ziganshin, Marat A.,Ziganshina, Sufia A.
, (2020/08/22)
The possibility of using fast scanning calorimetry (FSC) to study the kinetics of the solid-state cyclization of dipeptide was demonstrated in the present work for the first time. The activation energy and Arrhenius constant of the cyclization of L/
Anti-biofilm and anti-adherence properties of novel cyclic dipeptides against oral pathogens
Simon, Ga?lle,Bérubé, Christopher,Voyer, Normand,Grenier, Daniel
, p. 2323 - 2331 (2018/12/11)
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.
Thermally Induced Self-Assembly and Cyclization of l -Leucyl- l -Leucine in Solid State
Ziganshin, Marat A.,Safiullina, Aisylu S.,Gerasimov, Alexander V.,Ziganshina, Sufia A.,Klimovitskii, Alexander E.,Khayarov, Khasan R.,Gorbatchuk, Valery V.
, p. 8603 - 8610 (2017/09/22)
Thermal treatment of oligopeptides is one of the methods for synthesis of organic nanostructures. However, heating may lead not only to self-assembly of the initial molecules, but also to chemical reactions resulting in the formation of new unexpected nan
Interfacial supramolecular biomimetic epoxidation catalysed by cyclic dipeptides
Bérubé, Christopher,Barbeau, Xavier,Cardinal, Sébastien,Boudreault, Pierre-Luc,Bouchard, Corinne,Delcey, Nicolas,Lagüe, Patrick,Voyer, Normand
, p. 330 - 349 (2017/03/15)
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.
Biomimetic epoxidation in aqueous media catalyzed by cyclic dipeptides
Bérubé, Christopher,Voyer, Normand
supporting information, p. 395 - 403 (2016/04/05)
We have developed a practical epoxidation of electron-deficient enones in aqueous media using cyclic dipeptides as bioinspired green catalyst. Optimizing the reaction conditions in a triphasic system led to efficient conditions providing epoxides with good enantioselectivities. Depending on the catalyst substituent chirality, both enantiomers are obtained. The cyclic rigidity impacts significantly the enantioselectivity.
Novel chiral N,N′-dimethyl-1,4-piperazines with metal binding abilities
Bérubé, Christopher,Cardinal, Sébastien,Boudreault, Pierre-Luc,Barbeau, Xavier,Delcey, Nicolas,Giguère, Martin,Gleeton, Dave,Voyer, Normand
, p. 8077 - 8084 (2015/12/30)
With the objective of developing novel chiral ligands, we report an efficient strategy to prepare chiral N,N-dimethyl-1,4-piperazines, six-member heterocyclic molecules that possess metal binding features. We prepared and characterized 18 piperazines, and evaluated their ability to complex different mono- and divalent metals, using a rapid picrate extraction technique. Some newly prepared diamine ligands were used in diethylzinc alkylation of aryl aldehydes. Yields increased significantly in the presence of the diamine ligands, though enantioselectivity was low. The results demonstrate the validity of the approach for preparing and identifying useful chiral diamine ligands.
Cyclic dipeptides exhibit potency for scavenging radicals
Furukawa, Tadashi,Akutagawa, Takashi,Funatani, Hitomi,Uchida, Toshikazu,Hotta, Yoshihiro,Niwa, Masatake,Takaya, Yoshiaki
, p. 2002 - 2009 (2012/05/04)
Twenty kinds of cyclic dipeptides containing l-leucine were synthesized, and their antioxidant activity against .OH and O2·- was investigated. Compounds possessing polar amino acid residues, such as Asp, Cys, Glu, Lys, Pro, Ser, and Trp, exhibited higher antioxidant activity against .OH than vitamin E. However, only cyclo(l-Cys-l-Leu) scavenged O2·-.
Cyclic dipeptides: Catalyst/promoter-free, rapid and environmentally benign cyclization of free amino acids
Nonappa,Ahonen, Kari,Lahtinen, Manu,Kolehmainen, Erkki
supporting information; experimental part, p. 1203 - 1209 (2011/06/26)
"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
Cao, Yanchun,Cao, Shuxia,Xie, Yali,Zong, Xiangkun,Zhao, Yufen
experimental part, p. 1173 - 1179 (2012/04/23)
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
Synthesis of peptides and pyrazines from β-amino alcohols through extrusion of h2 catalyzed by ruthenium pincer complexes: Ligand-controlled selectivity
Gnanaprakasam, Boopathy,Balaraman, Ekambaram,Ben-David, Yehoshoa,Milstein, David
supporting information; experimental part, p. 12240 - 12244 (2012/01/30)
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
