L-2-Indanylglycine is an L-configured, non-proteinogenic amino acid derivative featuring a glycine backbone substituted at the 2-position with an indanyl (indane) side chain. The molecule bears a free amino group and a free carboxyl group, with the bulky, hydrophobic indane substituent providing conformational constraint and altered polarity compared with simple aliphatic amino acids. In peptide chemistry and chemical biology, it is used as a building block to introduce a hydrophobic, sterically defined residue into peptide analogues for structure-activity studies, conformational probing, and synthetic labeling strategies where a non-natural amino acid side chain is required.
CAT No: CP21901
L-2-Indanylglycine is an L-configured amino acid derivative in which the glycine backbone is substituted at the alpha position by a bulky indane (2-indanyl) group, creating a chiral center that strongly influences steric and conformational behavior. The molecule contains a primary amino functionality and a carboxylic acid group (or their protected equivalents depending on the supplied form), enabling standard amino acid coupling chemistry while also providing a hydrophobic, rigid side-chain surrogate that can modulate peptide backbone dynamics. The indane substituent is nonpolar and conformationally constrained, which can affect solubility, aggregation propensity, and binding-site fit in peptide and peptidomimetic contexts. L-2-Indanylglycine therefore functions as a stereodefined chiral building block and synthetic intermediate for preparing substituted amino acid derivatives and peptide analogs with altered hydrophobicity and steric profiles.
1. Peptide Synthesis
L-2-Indanylglycine is used in peptide synthesis and peptide building block preparation to introduce a rigid indane-bearing side chain at a glycine-adjacent position, supporting the construction of constrained peptide sequences and peptidomimetic scaffolds. The amino and carboxyl functionalities participate in peptide coupling chemistry, while the L-stereochemistry provides stereochemical control at the substituted alpha center. Protecting-group strategies for the amine and carboxyl (for example, N-protection and temporary carboxyl activation) can be employed to enable selective coupling and subsequent deprotection steps during solid-phase or solution-phase assembly. Downstream peptide analogs prepared from this amino acid can be used to probe how hydrophobic bulk and conformational restriction influence folding, receptor recognition, or protease susceptibility in structure-activity relationship studies.
2. Peptidomimetics And SAR
L-2-Indanylglycine is applied in peptidomimetic construction and SAR studies where incorporation of a nonpolar, sterically demanding indane substituent can tune molecular recognition and conformational preferences. The rigid indane group can serve as a side-chain surrogate that changes local hydrophobic contacts and steric shielding around the peptide backbone, while the L-configuration preserves defined stereochemical presentation. Derivatization of the amino acid through N-functionalization or carboxyl activation can enable rapid generation of analog libraries for comparative evaluation in medicinal chemistry workflows. The resulting substituted peptide-like molecules can be used as chemical probes or lead-optimization intermediates to map structure-function relationships driven by hydrophobicity and stereochemical geometry.
3. Chiral Building Block Synthesis
L-2-Indanylglycine is employed as a chiral amino acid intermediate for stereoselective synthesis of substituted derivatives and downstream chiral fragments used in fine chemical synthesis. The alpha stereocenter adjacent to the amino and carboxyl groups provides a defined three-dimensional scaffold for further functional group transformation, including conversion to protected amino acid derivatives, esterification for handling, or activation for subsequent coupling. The indane substituent can withstand many peptide-manipulation conditions and can be carried through multi-step sequences as a stable hydrophobic motif. Chiral derivatives derived from L-2-Indanylglycine can be incorporated into larger chiral intermediates for process chemistry routes that require stereochemical fidelity across sequential transformations.
4. Side-Chain Functionalization
L-2-Indanylglycine is suitable for side-chain functionalization and amino acid derivatization strategies that generate new handles for conjugation, tagging, or scaffold diversification. The amino functionality can be protected, alkylated, acylated, or converted into activated forms that support selective downstream reactions, while the carboxylic acid can be transformed into esters, amides, or coupling-ready intermediates. The indane-bearing hydrophobic region can influence reactivity by affecting local polarity and solvation, which can be relevant when designing derivatization steps that must remain compatible with other functional groups. Functionalized derivatives can be used to prepare labeled amino acid analogs, conjugatable intermediates, or specialized peptide building blocks for chemical biology and analytical research.
5. Chemical Biology Probes
L-2-Indanylglycine is utilized in chemical biology research as a stereodefined component for designing peptide-based probes that interrogate biomolecular interactions. The combination of an amino acid backbone and a rigid hydrophobic indane substituent can be incorporated into ligands to modulate binding-site complementarity and to control local conformational behavior in protein-binding assays. Protecting-group control of the amine and carboxyl groups supports sequential assembly of probe molecules and maintenance of stereochemistry during synthesis. L-2-Indanylglycine-derived peptide analogs can serve as research intermediates for studying binding determinants, mapping interaction hotspots, and generating tool compounds for biochemical characterization.
6. Pharmaceutical Intermediate Preparation
L-2-Indanylglycine is applied in pharmaceutical intermediate preparation and process chemistry intermediate design where substituted amino acid derivatives are required for manufacturing-compatible routes to peptide-like active ingredients or intermediates. The amino acid functional group set enables conversion into protected amino acid forms that are amenable to scalable peptide coupling steps, while the indane substituent provides a hydrophobic, conformationally restricted motif that can be carried through late-stage synthesis. Carboxyl activation and N-protection/deprotection strategies can be aligned with robust synthetic sequences to generate defined stereochemical intermediates for downstream assembly. Industrially relevant use can include preparation of chiral, substituted building blocks that support fine chemical synthesis of peptidomimetic compounds and related specialty intermediates.
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