10.1039/b411545g
The study investigates the effects of side chain homologation on the pairing selectivity and stacking of alanyl peptide nucleic acids (alanyl-PNAs), which are oligomers based on a regular peptide backbone with covalently linked nucleobases. The researchers compared different linkers, such as methylene (alanyl-PNA), ethylene (homoalanyl-PNA), and trimethylene (norvalyl-PNA), to understand how side chain length influences pairing selectivity and base pair stacking. The chemicals used in the study included various nucleo amino acids, such as alanine, homoalanine, and norvaline, which were prepared and oligomerized to form different PNA sequences. These sequences were then tested for their pairing properties and stabilities, allowing the researchers to draw conclusions about the interdependence between recognition, insertion of methylene groups, and the backbone topology. The purpose of these chemical modifications was to selectively manipulate pairing selectivity and base pair stacking, providing insights into the recognition interactions and potential applications of PNAs in molecular biology.
10.1055/s-0039-1690705
The study presents a stereoselective synthesis method for three enantiomerically pure non-proteinogenic amino acids: L-norvaline, γ-oxonorvaline, and syn-γ-hydroxynorvaline. These amino acids were synthesized using a chromatography-free route that leverages a highly diastereoselective crystallization-driven Mannich reaction. Key chemicals used in the study include acetone, glyoxylic acid monohydrate, and (S)-(4-methoxyphenyl)ethylamine, which serve as readily available building blocks for the synthesis. The process involves chemoselective and stereoselective reductions of a key intermediate, amino ketone 4, to access the target amino acids. The study highlights the use of inexpensive reagents, simple protocols, and excellent selectivity, with no need for chromatography, making it an efficient and environmentally friendly approach to synthesize these biologically significant compounds.