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Relevant academic research and scientific papers

Asymmetric synthesis, biological activity and molecular docking studies of some unsaturated α-amino acids, derivatives of glycine, allylglycine and propargylglycine

New enantiomerically enriched unsaturated tailor-made amino acids have been obtained. As a starting amino acid synthon for the asymmetric synthesis of tailor-made unsaturated amino acids, Ni(II) square-planar complexes of Schiff's bases of propargylglycine, allylglycine and glycine with chiral auxiliary (S)-2-N-(N’-benzylprolyl)-aminobenzophenone ((S)-BPB) were used. The Cα-alkylation of propargylglycine, allylglycine and glycine moieties resulted in the asymmetric synthesis of novel (S)-α-propargylglycine, (S)-α-allylglycine and glycine derivatives containing an aromatic group in the side chain (de 80–95,5%). After purification and cleavage of the metal complexes, the amino acids were isolated in high enantiomeric purity (ee >99%). Of the obtained seven tailor-made amino acids four showed inhibitory activity to collagenase G. The amino acid with an acetylene bond in the side chain (IC50 = 1.29 ± 0.02 mM) had the best result. Molecular docking showed that the amino acids with activity to collagenase G contained hydrogen and π-π bonds with the enzyme.

Synthesis of enantiomerically enriched non-protein α-amino acids and their study as aldose reductase inhibitors

Ni(II) complexes of the Schiff base of the chiral auxiliary (S)-2-N-(N′-benzylprolyl)aminobenzophenone (BPB) and α-substituted propargylglycines as the initial complexes in the Glaser reaction were investigated. Three new bis-derivatives of propargylglycine were obtained with high chemical yields. To study the patterns of biological activity of the structure of bis-derivatives of propargylglycine, mono analogs of these amino acids were obtained. Bis-derivative of propargylglycine selectively inhibited ALR2 while did not inhibit ALR1. Thus,?(2S,9S)-2,9-diamino-2,9-bis(2-chlorobenzyl)deca-4,6-diynedioic selectively inhibited ALR2 with IC50 = 0.335 mM, while (S)-2-(2-chlorobenzyl)-2-aminopent-4-ynoic and (2S,9S)-2,9-diamino-2,9-bis(3-fluorobenzyl)deca-4,6-diynedioic acids showed inhibitory effect on ALR1 with IC50 = 0.49 mM and IC50 = 0.289 mM, respectively. The results of docking analysis indicated that both amino acids demonstrated the ability to form bonds with different functional groups of the enzyme. We assume that some amino acids of nonfunctional groups, such as Trp20 of ALR2, can play a key role in inhibitor–enzyme interactions.

OPTICALLY ACTIVE QUATERNARY AMMONIUM SALT HAVING AXIAL ASYMMETRY AND PROCESS FOR PRODUCING ALPHA-AMINO ACID AND DERIVATIVE THEREOF WITH THE SAME

The present invention provides a compound of the following formula (I) below. This compound (I) can be produced by reacting a 2,2'-dimethylene bromide-1,1'-binaphthyl derivative, which can be produced by a relatively small number of processes, with an eas