This review provides a fresh overview of non-canonical amino acids and their applications in the design of peptidomimetics. Non-canonical amino acids appear widely distributed in nature and are known to enhance the stability of specific secondary structures and/or biological function. Contrary to the ubiquitous DNA-encoded amino acids, the structure and function of these residues are not fully understood. Here, results from experimental and molecular modelling approaches are gathered to classify several classes of non-canonical amino acids according to their ability to induce specific secondary structures yielding different biological functions and improved stability. Regarding side-chain modifications, symmetrical and asymmetrical α,α-dialkyl glycines, Cα to Cα cyclized amino acids, proline analogues, β-substituted amino acids, and α,β-dehydro amino acids are some of the non-canonical representatives addressed. Backbone modifications were also examined, especially those that result in retro-inverso peptidomimetics and depsipeptides. All this knowledge has an important application in the field of peptidomimetics, which is in continuous progress and promises to deliver new biologically active molecules and new materials in the near future.
The appearance and quick spread of the new severe acute respiratory syndrome coronavirus disease, COVID-19, brought major societal challenges. Importantly, suitable medical diagnosis procedures and smooth clinical management of the disease are an emergent need, which must be anchored on novel diagnostic methods and devices. Novel molecular diagnostic tools relying on nucleic acid amplification testing have emerged globally and are the current gold standard in COVID-19 diagnosis. However, the need for widespread testing methodologies for fast, effective testing in multiple epidemiological scenarios remains a crucial step in the fight against the COVID-19 pandemic. Biosensors have previously shown the potential for cost-effective and accessible diagnostics, finding applications in settings where conventional, laboratorial techniques may not be readily employed. Paper- and cellulose-based biosensors can be particularly relevant in pandemic times, for the renewability, possibility of mass production with sustainable methodologies, and safe environmental disposal. In this review, paper-based devices and platforms targeting SARS-CoV-2 are showcased and discussed, as a means to achieve quick and low-cost PoC diagnosis, including detection methodologies for viral genomic material, viral antigen detection, and serological antibody testing. Devices targeting inflammatory markers relevant for COVID-19 are also discussed, as fast, reliable bedside diagnostic tools for patient treatment and follow-up.
Iminosugars continue receiving a great deal of attention from chemists and biochemists for their potential as pharmaceutics. This is a comprehensive review of the methods found in the literature for the synthesis of piperidine, pyrrolidine, indolizidine, and pirrolizidine iminosugars, starting from D/L-erythrose and D/L-threose carbon chains (tetroses). This review shows the crescent popularity of small molecules to build up iminosugar molecules. Methodologies described herein utilize inexpensive commercial materials. The synthesis of the four tetroses is included referring old and modern methodologies.
5-(5-Aminoimidazol-4-yl)-1,2,4-triazol-3-ones were obtained under mild experimental conditions from 5-amino-4-(N-ethoxycarbonyl) cyanoformimidoyl imidazoles and hydrazine in a rapid one-pot reaction. When hydroxylamine hydrochloride was used, in the presence of base, the corresponding 1,2,4-oxadiazol-5-ones were isolated. An equally fast reaction occurred when 5-amino-4-(N-acetyl/benzoyl) cyanoformimidoyl imidazoles were combined with hydrazine to give 5-(5-aminoimidazol-4-yl)-1,2,4-triazoles.
29 December 2016 in The Journal of Organic Chemistry