L-Octahydroindole-2-carboxylic acid is a cyclic, non-aromatic amino acid featuring an octahydroindole ring system with a carboxylic acid at the 2-position, classifying it as a substituted amino acid suitable for incorporation into peptide-like structures. The molecule presents both an amino group and a carboxyl group, with the ring-constrained framework providing a rigid side-chain environment that can influence conformational preferences in synthesized peptides, while the "L" designation indicates the specified stereochemical form at the amino acid center. In research and synthetic chemistry, it is used as a defined amino acid building block for preparing modified peptides and peptidomimetics and for structure-activity or conformational studies where a constrained cyclic side chain is required.
CAT No: CP27497
CAS No:80875-98-5
Synonyms/Alias:80875-98-5;(2S,3aS,7aS)-octahydro-1H-indole-2-carboxylicacid;L-Octahydroindole-2-carboxylicacid;(2S,3AS,7AS)-2-Carboxyoctahydroindole;(2S,3aS,7aS)-Octahydroindole-2-carboxylicacid;(2S,3aS,7aS)-2-Carboxyperhydroindole;UNII-9ID44U804I;(2S,3AS,7AS)-PERHYDROINDOLE-2-CARBOXYLICACID;1H-Indole-2-carboxylicacid,octahydro-,(2S,3aS,7aS)-;(2S,3aS,7aS)-2,3,3a,4,5,6,7,7a-octahydro-1H-indole-2-carboxylicacid;hydroindole;Octahydroindole-2-CarboxylicAcid;AC1OLREW;PubChem15646;H-OIC-OH;L-OIC-OH;AC1Q71AB;KSC448A4B;SCHEMBL1414979;(2S,3aS,7aS)-2-carboxyocta;CTK3E8040;CQYBNXGHMBNGCG-FXQIFTODSA-N;MolPort-003-849-652;9ID44U804I;HMS1759A13
L-Octahydroindole-2-carboxylic acid is a chiral, cyclic amino acid with an octahydroindole (bicyclic) ring system that constrains side-chain conformation and presents a stereogenic center at the alpha carbon. The molecule bears a carboxylic acid functional group and a secondary amine embedded in a saturated heterocycle framework, enabling amino-acid type coupling chemistry while maintaining a rigid, conformationally biased scaffold. As a free amino acid, it participates in standard protection and activation strategies used for peptide building blocks, including conversion to N-protected derivatives and formation of activated carboxylic acid intermediates. The saturated bicyclic structure can influence amide-bond formation, conformational preferences in peptide analogs, and downstream derivatization routes used in synthetic and biochemical research.
1. Peptide Synthesis
L-Octahydroindole-2-carboxylic acid is applied in peptide synthesis and peptidomimetic construction where a conformationally constrained cyclic residue is required. The alpha-carboxylic acid and alpha-amino functionality support conversion to coupling-ready protected amino acid derivatives, while the rigid octahydroindole ring can modulate local backbone geometry in the resulting amide chain. N-protection of the amino group and activation of the carboxyl group can be used to enable peptide coupling under common peptide chemistry workflows, including incorporation into short peptide sequences and structure-defined analog libraries. Downstream, the resulting peptide products can serve as scaffold components for synthetic methodology development and conformational studies in amino acid chemistry.
2. Side-Chain Functionalization
L-Octahydroindole-2-carboxylic acid is used for side-chain functionalization and synthetic organic chemistry intermediate design, leveraging the saturated bicyclic framework as a stable chiral platform. The amino acid core provides a handle for selective protection/deprotection cycles, allowing orthogonal transformations that can be directed toward ring-substituted derivatives or carboxyl-activated forms for subsequent coupling. Carboxylic acid derivatization into esters or activated acids supports downstream attachment to electrophiles or coupling partners, while the embedded heterocycle can tolerate a range of functional group manipulations typical of process chemistry intermediate preparation. Resulting functionalized derivatives can be employed to build larger heterocyclic architectures or to generate stereodefined intermediates for medicinal chemistry and materials-oriented synthesis.
3. Chiral Building Block Development
L-Octahydroindole-2-carboxylic acid is suitable as a chiral amino acid intermediate in asymmetric synthesis and chiral building block development where rigid stereochemistry is a design requirement. The defined L-configuration at the alpha carbon provides stereochemical control during conversion to N-protected amino acid derivatives and activated carboxylic acid intermediates used for stereospecific coupling. The cyclic octahydroindole scaffold can be retained through protected amino acid synthesis, supporting the preparation of enantiopure fragments for peptide analogs, receptor-binding probes, or conformationally restricted stereochemical elements. Downstream synthetic utility includes use as a starting material for chiral fragment assembly in fine chemical synthesis and industrial route planning for stereodefined products.
4. Chemical Biology Probes
L-Octahydroindole-2-carboxylic acid is applied in chemical biology research for constructing conformationally biased peptide-like probes and biomolecule-interacting scaffolds. The amino acid functionality enables incorporation into labeled or reactive peptide constructs after conversion to protected building blocks, while the rigid bicyclic ring can influence binding-site recognition by constraining accessible conformations. Carboxyl activation and amide formation allow attachment to linkers, tags, or affinity handles, supporting workflows that require controlled spatial presentation of functional groups. Resulting cyclic amino acid-containing probes can be utilized in molecular recognition studies, protein-interaction mapping, and structure-activity relationship investigations of peptide-derived ligands.
5. Pharmaceutical Intermediate Preparation
L-Octahydroindole-2-carboxylic acid is used in pharmaceutical intermediate preparation and process chemistry intermediate development where a stereodefined cyclic amino acid residue is required for downstream synthesis. The free carboxylic acid and amino group support manufacturing-compatible protection strategies and conversion to coupling-ready derivatives that can be carried through multi-step sequences without racemization under appropriate conditions. The octahydroindole ring system can function as a conformational constraint within peptidomimetic or small-molecule frameworks, enabling the generation of analog series for medicinal chemistry programs. Downstream, protected and activated derivatives derived from this amino acid can serve as key intermediates for producing larger drug-like scaffolds and for assembling structure-defined libraries in specialty chemical production.
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