35373-95-6Relevant academic research and scientific papers
Pd-Catalysed oxidative carbonylation of α-amino amides to hydantoins under mild conditions
Botla, Vinayak,Carfagna, Carla,Della Ca, Nicola,Gabriele, Bartolo,Maestri, Giovanni,Mancuso, Raffaella,Montanari, Luca,Motti, Elena,Voronov, Aleksandr
supporting information, p. 294 - 297 (2022/01/06)
The first example of palladium-catalysed oxidative carbonylation of unprotected α-amino amides to hydantoins is described here. The selective synthesis of the target compounds was achieved under mild conditions (1 atm of CO), without ligands and bases. The catalytic system overrode the common reaction pathway that usually leads instead to the formation of symmetrical ureas.
Antimicrobial and antitumor activity of peptidomimetics synthesized from amino acids
Li, Huan,Fu, Shuang,Wang, Yudan,Yuan, Xuan,Liu, Lijia,Dong, Hongxing,Wang, Qiang,Zhang, Zhijia
, (2020/12/07)
Thirteen cationic peptidomimetics derived from amino acids bearing an alkyl or ethynylphenyl moiety that mimic the structure of cationic antibacterial peptides were designed and synthesized using a simple coupling reaction of an amino acid with a substitu
Pore-Forming Monopeptides as Exceptionally Active Anion Channels
Ren, Changliang,Zeng, Fei,Shen, Jie,Chen, Feng,Roy, Arundhati,Zhou, Shaoyuan,Ren, Haisheng,Zeng, Huaqiang
supporting information, p. 8817 - 8826 (2018/07/05)
We describe here a unique family of pore-forming anion-transporting peptides possessing a single-amino-acid-derived peptidic backbone that is the shortest among natural and synthetic pore-forming peptides. These monopeptides with built-in H-bonding capacity self-assemble into an H-bonded 1D columnar structure, presenting three types of exteriorly arranged hydrophobic side chains that closely mimic the overall topology of an α-helix. Dynamic interactions among these side chains and membrane lipids proceed in a way likely similar to how α-helix bundle is formed. This subsequently enables oligomerization of these rod-like structures to form ring-shaped ensembles of varying sizes with a pore size of smaller than 1.0 nm in diameter but sufficiently large for transporting anions across the membrane. The intrinsic high modularity in the backbone further allows rapid tuning in side chains for combinatorial optimization of channel's ion-transport activity, culminating in the discovery of an exceptionally active anion-transporting monopeptide 6L10 with an EC50 of 0.10 μM for nitrate anions.
Combinatorial Evolution of Fast-Conducting Highly Selective K+-Channels via Modularly Tunable Directional Assembly of Crown Ethers
Ren, Changliang,Shen, Jie,Zeng, Huaqiang
supporting information, p. 12338 - 12341 (2017/09/23)
We describe here a modularly tunable molecular strategy for construction and combinatorial optimization of highly efficient K+-selective channels. In our strategy, a highly robust supramolecular H-bonded 1D ensemble was used to order the appended crown ethers in such a way that they roughly stack on top of each other to form a channel for facilitated ion transport across the membrane. Among 15 channels that all prefer K+ over Na+ ions, channel molecule 5F8 shows the most pronounced optimum for K+ while disfavoring all other biologically important cations (e.g., Na+, Ca2+ and Mg2+). With a K+/Na+ selectivity of 9.8 and an EC50 value of 6.2 μM for K+ ion, 5F8 is clearly among the best synthetic potassium channels developed over the past decades.
Ribozymomimetic chemical synthesis of peptide bond using phosphorous acid/oxirane mediators
Bayryamov,Danalev,Vassilev
experimental part, p. 338 - 344 (2011/04/24)
Chemical Equation Presented A model system is created that mimics natural ribosome as well as the way of ribozyme action. It uses oxirane analogue as condensation reagent and H3PO3 as activator for the carboxyl group and as protecting reagent for the NH2
Organocatalyzed highly enantioselective michael additions of malonates to enones by using novel primary-secondary diamine catalysts
Yang, Ying-Quan,Zhao, Gang
supporting information; experimental part, p. 10888 - 10891 (2009/10/02)
A novel primary-secondary diamine catalyst readily available from primary amino acids in three steps for the highly enantioselective Michael additions of malonates to α,β-unsaturated ketones was reported. The Michael reaction of dimethyl malonate with benzylideneacetone was selected as a model reaction for catalyst evaluation. The length of the alkyl chain is found to influence the catalytic abilities of the catalysts and the n-propylated catalyst gave the highest yield and ee value. The addition of a series of malonates to enone performed under the optimized conditions is found to be sensitive to the steric hinderance on the malonates. Heterocyclic furan enone is found to perform well to give the desired product in 92% yield and 99% ee, while no decrease in yield and ee value is observed for sterically hindered enone.
Synthesis of hydantoins from enantiomerically pure α-amino amides without epimerization
Zhang, Dun,Xing, Xuechao,Cuny, Gregory D.
, p. 1750 - 1753 (2007/10/03)
A method for the preparation of enantiomerically pure hydantoins from optically pure α-amino amides utilizing triphosgene is described. We also propose that the racemization observed with 1,1′-carbonyldiimidazole (CDI) for this type of reaction is due to
