D-2-Indanylglycine is a D-configured, non-proteinogenic amino acid derivative featuring an indane (2-indanylmethyl) side chain attached to the alpha carbon, classifying it as a glycine analogue with a bulky, hydrophobic substituent rather than a hydrogen side chain. The molecule contains a free amino group and a free carboxyl group on the alpha carbon, with the stereocenter specified as D, which influences conformational preferences and side-chain packing in peptide-like structures. D-2-Indanylglycine is used in peptide synthesis and structure-activity studies where incorporation of an indane-bearing residue provides a chemically defined steric and hydrophobic element for mapping sequence-dependent effects, as well as in analytical method development for amino acid derivative profiling.
CAT No: CP21902
D-2-Indanylglycine is a chiral amino acid derivative featuring a glycine backbone bearing a stereogenic 2-indanyl substituent, giving a defined D-configuration at the alpha carbon. The molecule contains a primary amine and a carboxylic acid (or, depending on supplier form, corresponding salt/derivative), with the indane ring system providing a rigid, hydrophobic side-chain analog that can influence conformational bias in peptides and peptidomimetics. The amine and acid functional groups support standard amino acid coupling chemistry, while the aromatic-like indane scaffold can participate in hydrophobic contacts and π-associated interactions in binding studies. D-2-Indanylglycine is commonly handled as a chiral synthetic intermediate and peptide-building block precursor for downstream derivatization, stereoselective synthesis, and side-chain functional modification strategies.
1. Peptide Synthesis
D-2-Indanylglycine is used in peptide coupling chemistry to introduce a conformationally constrained, hydrophobic residue into peptide sequences and peptide analogs. The amino acid functionality enables formation of amide bonds through standard protected-amino-acid strategies, where the carboxyl group is activated and the amine is protected as needed to control chemoselectivity. The D-stereocenter can be retained during peptide assembly to generate stereochemically defined analogs for structure-activity relationship studies. Incorporation into short peptides, cyclic scaffolds, or backbone-modified constructs supports downstream deprotection and purification workflows typical of peptide synthesis and medicinal chemistry intermediate preparation.
2. Chiral Building Block Synthesis
D-2-Indanylglycine serves as a chiral amino acid intermediate for stereoselective synthesis of D-configured derivatives and chiral auxiliaries. The rigid indanyl side-chain can be leveraged to create stereochemically informative products, including N-protected amino acid derivatives, activated esters, and coupling-ready intermediates for fine chemical synthesis. The primary amine and carboxylic acid enable orthogonal protection and selective transformations, supporting controlled conversion to amides, esters, or peptide coupling reagents. Downstream, D-2-Indanylglycine-derived intermediates can be applied in asymmetric synthesis planning where retention or inversion of stereochemistry is a key design variable.
3. Peptidomimetic Construction
D-2-Indanylglycine is applied in peptidomimetic design to replace flexible glycine-like segments with a bulky, conformationally biased residue that can modulate backbone geometry and local steric environment. The indane scaffold provides a hydrophobic, rigid substituent that can enhance binding-site complementarity in receptor or enzyme interaction models without requiring additional aromatic substitution. The amino acid core supports sequential derivatization into N-alkylated, N-acyled, or C-terminal modified analogs, enabling exploration of steric and electronic effects on molecular recognition. Peptidomimetic constructs prepared from D-2-Indanylglycine can be advanced as research-grade scaffolds for SAR studies and molecular design campaigns.
4. Chemical Biology Probes
D-2-Indanylglycine is suitable for chemical biology research where amino acid incorporation into biomolecule-reactive constructs enables controlled labeling and functional modulation. The amine and carboxyl groups allow conversion into conjugation handles such as activated esters, amide-linked linkers, or protected intermediates that can be appended to targeting motifs. The D-configuration and indanyl hydrophobicity can influence cell-permeability-like properties and binding orientation in probe design, while maintaining compatibility with peptide-based delivery formats. Downstream derivatives can be used to generate standardized probe libraries, enabling comparative studies of labeling position, linker chemistry, and stereochemical effects in biochemical assays.
5. Pharmaceutical Intermediate Preparation
D-2-Indanylglycine is employed as a chiral building block in pharmaceutical intermediate preparation for manufacturing-oriented synthesis of amino acid derivatives and backbone-modified intermediates. The presence of both amine and carboxylic acid functionalities supports scalable protection-group strategies that are compatible with industrial peptide coupling and intermediate isolation practices. The indanyl side-chain can be carried through multi-step routes to furnish stereodefined intermediates used in active-ingredient precursor synthesis or in the generation of analog series for process development. The compound's role as a defined D-configured amino acid derivative supports consistent downstream transformations, including conversion to coupling reagents, ester intermediates, and protected amino acid forms used in fine chemical production.
6. Analytical Research Standards
D-2-Indanylglycine can be utilized in analytical research as a stereochemically defined standard for method development and impurity profiling in amino acid and peptide analysis. The distinct D-configuration and indanyl moiety provide a chromatographically and spectroscopically distinguishable signature when incorporated into derivatized forms or used as a reference material. Functional group interconversion to N-protected or esterified derivatives can support targeted analytical workflows for monitoring amino acid coupling efficiency, protecting-group stability, and stereochemical integrity. Downstream, D-2-Indanylglycine-derived standards and labeled or derivatized analogs can be applied to validate analytical selectivity across peptide building block preparation and peptide assembly processes.
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