(SR)-Indoline-2-carboxylic acid is a non-proteinogenic, cyclic amino acid derivative featuring an indoline ring bearing a carboxylic acid at the 2-position, with the (SR) stereochemical designation indicating a defined chiral relationship within the molecule. The structure contains both an amino functional group and a carboxyl group, enabling formation of amino acid salts and participation in peptide-coupling chemistry, while the fused aromatic heterocycle provides a rigid, hydrophobic side-chain environment distinct from proteinogenic amino acids. In synthetic and chemical biology workflows, it is used as a building block for preparing modified peptides and structure-activity probes where incorporation of a constrained indoline-containing residue can tune conformational properties and side-chain interactions.
CAT No: CP26049
CAS No:78348-24-0
Synonyms/Alias:Indoline-2-carboxylicacid;78348-24-0;(+/-)-Indoline-2-carboxylicacid;16851-56-2;2,3-dihydro-1H-indole-2-carboxylicacid;2-Indolinecarboxylicacid;QNRXNRGSOJZINA-UHFFFAOYSA-N;SBB028477;PubChem3035;ACMC-1BCSC;AC1L3AUN;indoline2-carboxylicacid;ACMC-209pi7;ACMC-209s9r;AC1Q5UW0;AC1Q74CS;SCHEMBL91080;KSC182O9D;CHEMBL23081;dl-indoline-2-carboxylicacid;1H-Indoline-2-carboxylicacid;(?)-2-Indolinecarboxylicacid;302244_ALDRICH;SCHEMBL14003020;(+)-indoline-2-carboxylicacid
Chemical Name:(SR)-Indoline-2-carboxylic acid, (SR)-2,3-Dihydroindole-2-carboxylic acid, 97%
(SR)-Indoline-2-carboxylic acid is a chiral, non-proteinogenic amino acid building block featuring an indoline ring fused to a carboxylic acid at the 2-position. Its (SR) stereochemical designation makes it a useful intermediate for preparing enantiomerically defined derivatives used in peptide and peptidomimetic research. The rigid, aromatic heterocycle side-chain provides a conformationally constrained scaffold that is frequently leveraged in medicinal chemistry programs to probe structure-activity relationships and to build constrained analogs.
1. Peptidomimetic Building Blocks
(SR)-Indoline-2-carboxylic acid is used by medicinal chemistry and chemical biology groups to construct peptidomimetic scaffolds where a constrained indoline-containing residue is needed to emulate or modulate backbone/side-chain geometry. Researchers incorporate this building block into short peptide analogs and constrained ligand frameworks during lead optimization, using the carboxylic acid functionality as the anchor for standard amino-acid coupling strategies in downstream synthesis. The heteroaromatic indoline motif is particularly valued when conformational restriction and aromatic/heteroatom presentation are important for binding-site engagement studies.
2. Pharmaceutical Intermediate Development
(SR)-Indoline-2-carboxylic acid serves as a practical pharmaceutical intermediate for the preparation of indoline-based small molecules and bioactive analogs in process chemistry and R&D synthesis workflows. Teams developing heterocycle-containing candidates often rely on this compound as a stereodefined starting point for further functionalization at the carboxyl group and on the indoline framework, enabling access to a range of derivatives used in SAR campaigns. Its defined chirality supports the production of consistent analog series where stereochemical integrity is required for meaningful structure-activity comparisons.
3. Chiral Synthesis And Analog Libraries
(SR)-Indoline-2-carboxylic acid is commonly used in chiral synthesis and analog library construction to generate stereochemically controlled series of indoline-containing amino-acid derivatives. Research groups building residue libraries for peptide-like ligands use the (SR) configuration to maintain defined stereochemistry across parallel syntheses, improving interpretability when comparing structure-activity outcomes. The rigid indoline ring also helps reduce conformational variability among analogs, which can be advantageous when mapping how side-chain stereochemistry and aromatic heterocycle features influence molecular recognition.
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