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Updated: Jun 5, 2025

Synthesis of Indoxyl-glycosides for Detection of Glycosidase Activities
Published on: May 27, 2015
On the Reactivity of (S)-Indoline-2-Carboxylic Acid
Fabiana Cordella1, Sophie Faure2, Claude Taillefumier2
1Dipartimento di Chimica e Chimica Industriale, Università di Pisa, Pisa, Italy.
Abstract:
(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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Relative Reactivity of Carboxylic Acid Derivatives
A key factor in assessing the reactivity of the acid derivatives is the basicity of the substituent or the leaving group. The lower the basicity of the leaving group, the higher the reactivity of the derivative. The basicity of the leaving group follows this order:
Halide ions < Acyloxy ions < Alkoxy ions < Amine ions
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3
Reactions of Carboxylic Acids: Introduction
Carboxylic Acids to Acid Chlorides
Preparation of Carboxylic Acids: Hydrolysis of Nitriles
Reactions of Acid Anhydrides