Ni(II) complex of the Schiff base of the chiral auxiliary (S)-2-N-(N′-benzylprolyl)aminobenzophenone (BPB) and dehydroalanine as the initial complex in the addition reaction was investigated. The obtained four new derivatives of α-alanine were investigated as inhibitors of aldose reductase. Only one of them: (S)-2-amino-3-[(4-methylbenzyl)amino]propanoic acid showed activity. It becomes a reason for studying the patterns of biological activity of the structure of α-amino acids. The results of docking analysis indicated that (S)-2-amino-3-[(4-methylbenzyl)amino]propanoic acid demonstrated the ability to form bonds with different functional groups of the enzyme which let us assume that some amino acids of nonfunctional groups, such as Trp²⁰ of ALR2, can play a key role in inhibitor–enzyme interactions. Received: 16 August 2022 Accepted after revision: 12 September 2022 Accepted Manuscript online: 12 September 2022 Article published online: 19 October 2022 © 2022. Thieme. All rights reserved Georg Thieme Verlag KG Rüdigerstraße 14, 70469 Stuttgart, Germany

An efficient method for the asymmetric synthesis of a-amino acids, containing furyl- and thiophenyl-substituted triazoles in their side-chain, is reported. The strategy relies on Michael addition of 3,4,5-substituted 1,2,4-triazoles to the C=C bond of chiral NiII complexes containing the Schiff base formed from dehydroamino acids (dehydroalanine and (E + Z)-dehydroaminobutyric acid) and from chiral auxiliaries, i. e. (S)-2-N-(N0-benzylprolyl)aminobenzophenone and (S)-2-N- (N0-2-chlorobenzylprolyl) aminobenzophenone. The reactions proceeded with good to very good diastereoselectivity. Hydrolysis of the diastereomeric mixtures of metal complexes afforded the enantiomerically pure a-amino acids with high enantiomeric excess (ee> 98%).