A synthesis of new enantiomerically enriched derivatives of (S)-α-aminopropionic acid, containing in the β-position 1,2,3-triazole groups coupled with a o-, m- and p-substituted phenyl residue, was developed based on Cu(I) catalyzed [3 + 2] cycloaddition of azides with alkynes. As the starting materials was used the square-planar Ni(II)complex of the Schiff base of propargylglycine with the chiral auxiliary BPB (Benzylprolylbenzophenone) and 1,4-substituted phenyl azides. The assignment of the (S)-absolute configuration of the α-carbon atom of the amino acid residue of the main diastereomeric complexes of the cycloaddition products was carried out on the basis of positive Cotton effects in the region of 480–580 nm of the circular dichroism spectra. The target amino acids were isolated from acid hydrolysates of diastereomeric complexes using ion-exchange demineralization and crystallization from aqueous ethanol. Additional confirmation of the absolute configuration and determination of the enantiomeric purity of the target amino acids were carried out by chiral HPLC analysis. As a result, seven new non-proteinogenic (S)-α-amino acids, containing in the β-position a 1,2,3-triazole moiety, were synthesized.

Artavazd S. Poghosyan

Emma A. Khachatryan

Anna F. Mkrtchyan

Volodya Mirzoyan

Anahit M. Hovhannisyan

Karapet R. Ghazaryan

Ela V. Minasyan

Peter Langer

Ashot S. Saghyan

Amino Acids

AMINO ACIDS 发表来自氨基酸和蛋白质研究所有领域的贡献：分析、分离、合成、生物合成、交联氨基酸、外消旋化/对映异构体、氨基酸修饰如磷酸化、甲基化、乙酰化、糖基化和非酶糖基化，生理学和病理生理学中的氨基酸，生物学，氨基酸类似物和衍生物，多胺，辐射氨基酸，肽，稳定同位素和氨基酸同位素。医学、食品化学、营养学、肠胃病学、肾病学、神经化学、药理学、兴奋性氨基酸等领域的应用只是所涵盖的部分主题。感兴趣的领域包括：生物化学、食品化学、营养学、神经病学、精神病学、药理学、肾病学、胃肠病学、微生物学

The journal "Amino Acids" publishes contributions from all areas of amino acid and protein research, including analysis, separation, synthesis, biosynthesis, cross-linking of amino acids, racemization/enantiomers, amino acid modifications such as phosphorylation, methylation, acetylation, glycosylation, and non-enzymatic glycosylation, as well as the role of amino acids in physiology and pathophysiology, biology, amino acid analogs and derivatives, polyamines, radiolabeled amino acids, peptides, stable isotopes, and amino acid isotopes. Applications in fields such as medicine, food chemistry, nutrition, gastroenterology, nephrology, neurochemistry, and pharmacology are just some of the topics covered. Areas of interest include biochemistry, food chemistry, nutrition, neurology, psychiatry, pharmacology, nephrology, gastroenterology, and microbiology.

《Amino Acids》期刊发表与氨基酸和蛋白质研究相关的各个领域的贡献，包括分析、分离、合成、生物合成、交联氨基酸、外消旋化/对映异构体、氨基酸修饰（如磷酸化、甲基化、乙酰化、糖基化和非酶糖基化）、生理学和病理生理学中的氨基酸、生物学、氨基酸类似物和衍生物、多胺、辐射氨基酸、肽、稳定同位素和氨基酸同位素等。该期刊涵盖的应用领域包括医学、食品化学、营养学、肠胃病学、肾病学、神经化学和药理学等。感兴趣的研究领域包括生物化学、食品化学、营养学、神经病学、精神病学、药理学、肾病学、胃肠病学和微生物学等。

Category	Quartile
生物学	3
生物学, 生化与分子生物学	3

Synthesis of enantiomerically enriched β-substituted analogs of (S)-α-alanine containing 1-phenyl-1H-1,2,3-triazole groups

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Journal Info

Category	Quartile
BIOCHEMISTRY & MOLECULAR BIOLOGY	3