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Methyl esters of 2-( N -hydroxycarbamimidoyl)benzoyl-substituted α -amino acids as promising building blocks in peptidomimetic synthesis: a comparative study
Monatshefte für Chemie - Chemical Monthly ( IF 1.7 ) Pub Date : 2018-10-20 , DOI: 10.1007/s00706-018-2293-9 Volodymyr A. Tkachuk , Olga V. Hordiyenko , Irina V. Omelchenko , Volodomir V. Medviediev , Axelle Arrault
![](//media.springernature.com/lw685/springer-static/image/art%3A10.1007%2Fs00706-018-2293-9/MediaObjects/706_2018_2293_Figa_HTML.png)
中文翻译:
2-(N-羟基氨基甲酰基)苯甲酰基取代的α-氨基酸的甲酯是拟肽合成中有希望的组成部分:对比研究
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更新日期:2018-10-20
Monatshefte für Chemie - Chemical Monthly ( IF 1.7 ) Pub Date : 2018-10-20 , DOI: 10.1007/s00706-018-2293-9 Volodymyr A. Tkachuk , Olga V. Hordiyenko , Irina V. Omelchenko , Volodomir V. Medviediev , Axelle Arrault
Abstract
An efficient and simple synthetic protocol for the synthesis of a number methyl esters of 2-(N-hydroxycarbamimidoyl)benzoyl-substituted (S)-α-amino acids via subsequent coupling and hydroxyamination of 2-cyanobenzamide derivatives has been developed. Comparative analysis of three pseudopeptide series based on 2-cyano- and 2-amidoxime-substituted benzoic acid and its pyridine and pyrazine counterparts has been provided and it has revealed a practical advantage of the benzoic acid derivatives due to their greater availability. The impact of the nitrogen atom in the aromatic ring on the trans/cis-amide equilibrium in the proline derivatives is discussed.Graphical abstract
![](http://media.springernature.com/lw685/springer-static/image/art%3A10.1007%2Fs00706-018-2293-9/MediaObjects/706_2018_2293_Figa_HTML.png)
中文翻译:
![](https://scdn.x-mol.com/jcss/images/paperTranslation.png)
2-(N-羟基氨基甲酰基)苯甲酰基取代的α-氨基酸的甲酯是拟肽合成中有希望的组成部分:对比研究
摘要
已经开发了通过随后的2-氰基苯甲酰胺衍生物的偶合和羟基胺化来合成2-(N-羟基氨基甲酰基)苯甲酰基取代的(S)-α-氨基酸的许多甲酯的有效而简单的合成方案。提供了对两种基于2-氰基和2-ox肟肟取代的苯甲酸的假肽系列及其吡啶和吡嗪对应物的比较分析,并且由于其可用性更高,因此显示了苯甲酸衍生物的实际优势。讨论了芳环中氮原子对脯氨酸衍生物中反式/顺式-酰胺平衡的影响。图形概要
![](http://media.springernature.com/lw685/springer-static/image/art%3A10.1007%2Fs00706-018-2293-9/MediaObjects/706_2018_2293_Figa_HTML.png)