关于 (S)-吲哚啉-2-羧酸的反应性。

IF 2.8 4区化学 Q2 CHEMISTRY, ANALYTICAL

Chirality Pub Date : 2024-12-16 DOI:10.1002/chir.70008

Fabiana Cordella, Sophie Faure, Claude Taillefumier, Gennaro Pescitelli, Elisa Martinelli, Giuseppe Alonci, Zhengming Liu, Gaetano Angelici

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摘要

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On the Reactivity of (S)-Indoline-2-Carboxylic Acid

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On the Reactivity of (S)-Indoline-2-Carboxylic Acid

(S)-Indoline-2-carboxylic acid (H-(2S)-Ind-OH) possesses the ability to influence the conformation of peptide bonds towards the cis amide isomer in polar solvents. However, its potential utilization as a conformational switch within long peptide sequences poses challenges due to its low reactivity and strong inclination to form diketopiperazines. The present study explores its reactivity under various conditions and proposes synthetic strategies to overcome these limitations. A series of H-(2S)-Ind-OH containing di- and tri-peptides have been efficiently synthesized and characterized, ready to be inserted in more complex and longer sequences.

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来源期刊

Chirality 医学-分析化学

CiteScore

4.40

自引率

5.00%

发文量

124

审稿时长

1 months

期刊介绍： The main aim of the journal is to publish original contributions of scientific work on the role of chirality in chemistry and biochemistry in respect to biological, chemical, materials, pharmacological, spectroscopic and physical properties. Papers on the chemistry (physiochemical, preparative synthetic, and analytical), physics, pharmacology, clinical pharmacology, toxicology, and other biological aspects of chiral molecules will be published.