A new Ir(III)-NHC catalyst is reported that shows remarkable activity in the N-alkylation of unprotected amino acids. The catalytic system gives excellent selectivity toward monoalkylated α-amino acids and a high degree retention stereochemistry. wide range nonnatural have been prepared. These compounds represent an array building blocks could be used for direct synthesis peptidomimetics. amino...

In this communication, we report the design, synthesis and in vitro antimicrobial activity of ultra short peptidomimetics. Besides producing promising antibacterial activities against Staphylococcus aureus and methicillin-resistant S. aureus (MRSA), the dipeptidomimetics exhibited high antifungal activity against C. neoformans with IC50 values in the range of 0.16-19 μg/mL. The most potent anal...

We have synthesised a novel oxanorbornene β-aminoacid derivative and employed it in a stereoselective Ugi reaction. Hypothesis regarding the mechanism taking place during the reaction have been made and validated through the determination of the relative and absolute configuration of the Ugi adducts. Use of the correct choice of solvents can increase stereoselection. The resulting bicyclic pept...

Since the discovery of Cu(I)-catalysed click chemistry, the field of peptidomimetics has expanded to include 1,4-connected 1,2,3-triazoles as useful peptide bond isosteres. Here, we report the synthesis of triazole-containing analogues of the naturally occurring tyrosinase inhibitor cyclo-[Pro-Val-Pro-Tyr] and show that the analogues retain enzyme inhibitory activity, demonstrating the effectiv...

The chemical similarity of antibacterial cyclic peptides and peptidomimetics was studied in order to identify new promising cyclic scaffolds. A large descriptor space coupled with cluster analysis was employed to digitize known antibacterial structures and to gauge the potential of new peptidomimetic macrocycles, which were conveniently synthesized by acylbenzotriazole methodology. Some of the ...

A coumarin-based prodrug system has been recently developed in our laboratory for the preparation of esterase-sensitive prodrugs of amines, peptides, and peptidomimetics. The drug release rates from this prodrug system were found to be dependent on the structural features of the drug moiety. In certain cases, the release can be undesirably slow for drugs that are secondary amines with relativel...

We describe the controlled and regioselective transition-metal-catalyzed C-H bond arylation of protected L-histidine with aryl halides as the coupling partner. Using this approach, a large number of C-2 arylated L-histidines have been synthesized with diverse substitutions bearing electron-donating and electron-withdrawing groups, in good to excellent yields. These synthetic amino acids possess...

beta-amino acids have been employed in the past as bifunctional building blocks in intramolecular Ugi multicomponent reactions to yield beta-lactam derivatives. By using 7-azabicyclo[2.2.1]heptane-2-carboxylic acid, a different outcome has been observed and rationalised. The final compounds are polyfunctionalised azabicyclic peptidomimetics, and further elaboration can be achieved exploiting an...

Peptides show great pharmaceutical potential as active drugs and diagnostics in several clinical areas such as endocrinology, urology, obstetrics, oncology, etc. and as functional excipients in drug delivery systems to overcome tissue and cellular membrane barriers (Nestor, 2009). From a pharmaceutical point of view, peptides are situated somewhere between classical organic drug substances and ...