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

共 50 条

[31] Chemistry and reactivity of carboxylic acid-containing surfaces
Fleischer, CA
McKenna, WP
Apai, G
JOURNAL OF ADHESION SCIENCE AND TECHNOLOGY, 1996, 10 (01) : 79 - 91
[32] ENANTIOSELECTIVE CATALYTIC BORANE REDUCTIONS OF ACHIRAL KETONES - SYNTHESES AND APPLICATION OF 2 CHIRAL BETA-AMINO ALCOHOLS FROM (S)-2-INDOLINE CARBOXYLIC-ACID
MARTENS, J
DAUELSBERG, C
BEHNEN, W
WALLBAUM, S
TETRAHEDRON-ASYMMETRY, 1992, 3 (03) : 347 - 350
[33] (2S)-1-Carbamoylpyrrolidine-2-carboxylic acid
Seijas, Luis E.
Delgado, Gerzon E.
Mora, Asiloe J.
Bahsas, Ali
Briceno, Alexander
ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY, 2007, 63 : O303 - O305
[34] Efficient route to (S)-azetidine-2-carboxylic acid
Futamura, Y
Kurokawa, M
Obata, R
Nishiyama, S
Sugai, T
BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 2005, 69 (10) : 1892 - 1897
[35] Preparation of (S)-piperazine-2-carboxylic acid, (R)-piperazine-2-carboxylic acid, and (S)-piperidine-2-carboxylic acid by kinetic resolution of the corresponding racemic carboxamides with stereoselective amidases in whole bacterial cells
Eichhorn, E
Roduit, JP
Shaw, N
Heinzmann, K
Kiener, A
TETRAHEDRON-ASYMMETRY, 1997, 8 (15) : 2533 - 2536
[36] Reactivity of radiata pine sapwood towards carboxylic acid anhydrides
Dawson, BSW
Franich, RA
Kroese, HW
Steward, D
HOLZFORSCHUNG, 1999, 53 (02) : 195 - 198
[37] Structure and reactivity in the hydrolyses of aliphatic carboxylic acid esters and chlorides
Regan, Andrew C.
Watt, C. Ian F.
JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 2007, 20 (03) : 180 - 189
[38] PHOTOCHEMICAL REACTIVITY OF FUROCOUMARIN-3-CARBOXYLIC ACID ESTER
OTSUKI, T
RATINER, B
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1988, 196 : 384 - ORGN
[39] In vitro reactivity of carboxylic acid-CoA thioesters with glutathione
Sidenius, U
Skonberg, C
Olsen, J
Hansen, SH
CHEMICAL RESEARCH IN TOXICOLOGY, 2004, 17 (01) : 75 - 81
[40] 1,1'-DIPHOSPHAFERROCENES - 2-CARBOXYLIC ACID-DERIVATIVES AND REACTIVITY AT PHOSPHORUS
DELAUZON, G
DESCHAMPS, B
MATHEY, F
NOUVEAU JOURNAL DE CHIMIE-NEW JOURNAL OF CHEMISTRY, 1980, 4 (11): : 683 - 689

← 1 2 3 4 5 →