952-43-2Relevant 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.
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.
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
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·-.
Peptide bond formation by aminolysin-A catalysis: A simple approach to enzymatic synthesis of diverse short oligopeptides and biologically active puromycins
Usuki, Hirokazu,Yamamoto, Yukihiro,Arima, Jiro,Iwabuchi, Masaki,Miyoshi, Shozo,Nitoda, Teruhiko,Hatanaka, Tadashi
supporting information; experimental part, p. 2327 - 2335 (2011/05/02)
A new S9 family aminopeptidase derived from the actinobacterial thermophile Acidothermus cellulolyticus was cloned and engineered into a transaminopeptidase by site-directed mutagenesis of catalytic Ser491 into Cys. The engineered biocatalyst, designated aminolysin-A, can catalyze the formation of peptide bonds to give linear homo-oligopeptides, hetero-dipeptides, and cyclic dipeptides using cost-effective substrates in a one-pot reaction. Aminolysin-A can recognize several C-terminal-modified amino acids, including the l- and d-forms, as acyl donors as well as free amines, including amino acids and puromycin aminonucleoside, as acyl acceptors. The absence of amino acid esters prevents the formation of peptides; therefore, the reaction mechanism involves aminolysis and not a reverse reaction of hydrolysis. The aminolysin system will be a beneficial tool for the preparation of structurally diverse peptide mimetics by a simple approach.
L-proline-catalyzed asymmetric michael addition of 2-oxindoles to enones: A convenient access to oxindoles with a quaternary stereocenter
Freund, Matthias H.,Tsogoeva, Svetlana B.
, p. 503 - 507 (2011/04/18)
A new organocatalytic approach for 1,4-conjugate addition of 2-oxindoles to α,β-unsaturated ketones using the combination of readily available and nonexpensive l-proline and achiral trans-2,5-dimethylpiperazine as catalytic system is provided. The reaction results in oxindole derivatives with vicinal quaternary and tertiary carbon centers in up to 99% yield and 91% ee. Georg Thieme Verlag Stuttgart.
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
