Search Results (4)

Peptides are in great demand in the pharmaceutical arena and a majority of these peptides contain 20 or more amino acids. They are infrequently synthesised using the fragment condensation approach. A key limitation in adopting this approach more commonly is that protected peptide fragments with high purity are often required prior to the final condensation steps. It is hypothesized that understanding the hydrophobic nature of the protected amino acids will assist with designing optimal fragment purification processes when needed. Whilst a myriad of hydrophobicity indices are reported in the literature for unprotected amino acids, the literature lacks any data regarding the protected amino acids which form the key precursor for the fragment condensation task. In this current study, hydrophobicity indices for protected amino acids with common α-amino and sidechain protecting groups were experimentally determined. Different positions for each amino acid within the peptide chain were considered, namely at the C-terminal and N-terminal as well as internal positions. These data give deep insights on the hydrophobicity of each amino acid with respect to its position in the peptide chain. The data acquired in this research facilitated the prediction of the retention time of protected peptide fragments with an uncertainty of less than ±1.5%. Full article

Melissa officinalis L. is a medicinal plant used worldwide for ethno-medical purposes. Today, it is grown everywhere; while it is known to originate from Southern Europe, it is now found around the world, from North America to New Zealand. The biological properties of this medicinal plant are mainly related to its high content of phytochemical (bioactive) compounds, such as flavonoids, polyphenolic compounds, aldehydes, glycosides and terpenes, among many other groups of substances. Among the main biological activities associated with this plant are antimicrobial activity (against fungi and bacteria), and antispasmodic, antioxidant and insomnia properties. Today, this plant is still used by society (as a natural medicine) to alleviate many other illnesses and symptoms. Therefore, in this perspective, we provide an update on the phytochemical profiling analysis of this plant, as well as the relationships of specific biological and pharmacological effects of specific phytochemicals. Currently, among the organic solvents, ethanol reveals the highest effectiveness for the solvent extraction of precious components (mainly rosmarinic acid). Additionally, our attention is devoted to current developments in the extraction and fractionation of the phytochemicals of M. officinalis, highlighting the ongoing progress of the main strategies that the research community has employed. Finally, after analyzing the literature, we suggest potential perspectives in the field of sustainable extraction and purification of the phytochemical present in the plant. For instance, some research gaps concern the application of cavitation-assisted extraction processes, which can effectively enhance mass transfer while reducing the particle size of the extracted material in situ. Meanwhile, membrane-assisted processes could be useful in the fractionation and purification of obtained extracts. On the other hand, further studies should include the application of ionic liquids and deep eutectic solvents (DES), including DESs of natural origin (NADES) and hydrophobic DESs (hDES), as extraction or fractionating solvents, along with new possibilities for effective extraction related to DESs formed in situ, assisted by mechanical mixing (mechanochemistry-based approach). Full article

A synthetic strategy for the preparation of two orthogonally protected methyl esters of the non-proteinogenic amino acid 2,3-l-diaminopropanoic acid (l-Dap) was developed. In these structures, the base-labile protecting group 9-fluorenylmethyloxycarbonyl (Fmoc) was paired to the p-toluensulfonyl (tosyl, Ts) or acid-labile tert-butyloxycarbonyl (Boc) moieties. The synthetic approach to protected l-Dap methyl esters uses appropriately masked 2,3-diaminopropanols, which are obtained via reductive amination of an aldehyde prepared from the commercial amino acid N^α-Fmoc-O-tert-butyl-d-serine, used as the starting material. Reductive amination is carried out with primary amines and sulfonamides, and the process is assisted by the Lewis acid Ti(OⁱPr)₄. The required carboxyl group is installed by oxidizing the alcoholic function of 2,3-diaminopropanols bearing the tosyl or benzyl protecting group on the 3-NH₂ site. The procedure can easily be applied using the crude product obtained after each step, minimizing the need for chromatographic purifications. Chirality of the carbon atom of the starting d-serine template is preserved throughout all synthetic steps. Full article

A concise and efficient one-pot synthesis of 3-functionalized 4-hydroxycoumarin derivatives via a three-component domino reaction of 4-hydroxycoumarin, phenylglyoxal and 3-arylaminocyclopent-2-enone or 4-arylaminofuran-2(5H)-one under catalyst-free and microwave irradiation conditions is described. This synthesis involves a group-assisted purification process, which avoids traditional recrystallization and chromatographic purification methods. Full article