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

被引：0

作者：

Cordella, Fabiana ^{[1
]}

Faure, Sophie ^{[2
]}

Taillefumier, Claude ^{[2
]}

Pescitelli, Gennaro ^{[1
]}

Martinelli, Elisa ^{[1
]}

Alonci, Giuseppe ^{[3
]}

Liu, Zhengming ^{[1
]}

Angelici, Gaetano ^{[1
]}

机构：

[1] Univ Pisa, Dipartimento Chim & Chim Industriale, Pisa, Italy

[2] Univ Clermont Auvergne, Clermont Auvergne INP, CNRS, ICCF, Clermont Ferrand, France

[3] Spin Off Univ Pavia, UB CARE S r l, Pavia, Italy

来源：

CHIRALITY | 2024年 / 36卷 / 12期

关键词：

(S)-indoline-2-carboxylic acid; peptide coupling reaction; sterically hindered amino acid; ASYMMETRIC HYDROGENATION; DIPHENYLALANINE; DIPEPTIDES;

D O I：

10.1002/chir.70008

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

(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.

引用

页数：10

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