DL-2-Indanylglycine is a non-proteinogenic amino acid derivative in which the α-amino acid backbone bears an indanyl (indanylglycine) substituent at the 2-position, giving a sterically constrained, bicyclic side chain relative to glycine. The molecule contains a free primary amino group and a free carboxyl group on the α-carbon and is supplied as the DL racemate, providing both stereochemical forms at the chiral center when present. In peptide and peptidomimetic synthesis, the indanyl side chain can be used to introduce hydrophobic bulk and conformational restriction, while the free amino and carboxyl functionalities support incorporation into amide-forming coupling strategies and subsequent structure-activity or stability studies of modified peptide frameworks.
CAT No: CP21903
DL-2-Indanylglycine is a DL mixture of an amino acid derivative bearing an indane (indanylglycine) side chain at the alpha carbon, giving a chiral center in the 2-position relative to the glycine-like backbone. The molecule contains a primary amino functionality and a carboxylic acid group (or their corresponding protected forms in synthetic workflows), enabling standard amino acid coupling chemistry while introducing a bulky, hydrophobic indane motif that can modulate conformational preferences. The indane ring can participate in hydrophobic and steric interactions during peptide or peptidomimetic assembly, and the amino acid framework can be protected as an N-protected intermediate to control chemoselectivity. As a chiral building block precursor in DL form, DL-2-Indanylglycine is commonly used to access substituted glycine analogs, generate peptide fragments, and support downstream transformations to amide, ester, or activated-carboxyl derivatives in applied synthetic chemistry.
1. Peptide Synthesis
DL-2-Indanylglycine is applied in peptide building block preparation where glycine-like backbone reactivity is combined with an indane-bearing side chain for sterically constrained peptide analogs. The amino acid functional set supports N-protection and C-terminal activation strategies, enabling peptide coupling to form amide bonds under standard protected amino acid synthesis conditions. The indane substituent can be used to probe sequence-dependent conformational effects in short peptides and to generate peptide fragments for solid-phase or solution-phase assembly. DL-2-Indanylglycine-derived residues can therefore serve as practical inputs for constructing peptidomimetic libraries and studying how hydrophobic bulk influences folding and molecular recognition.
2. Peptidomimetics And SAR
DL-2-Indanylglycine is used in peptidomimetic construction for structure-activity relationship studies where the indane motif acts as a hydrophobic, conformationally biasing substituent. The alpha-amino acid framework can be incorporated into analogs that retain amide linkage geometry while varying stereochemical composition, which is relevant for mapping stereochemical tolerance in SAR workflows. N-protected forms of DL-2-Indanylglycine can be coupled to diverse carboxylic acid partners to generate series of substituted glycine analogs for medicinal chemistry screening and SAR mapping. Downstream derivatization of the carboxyl group into activated esters or amides supports rapid scaffold diversification and analytical characterization of analog panels.
3. Chiral Resolution Inputs
DL-2-Indanylglycine is suitable as a chiral amino acid intermediate feedstock for stereochemical separation and downstream enantioenriched synthesis planning. The presence of a single stereogenic center at the 2-position allows conversion into separable derivatives through salt formation or formation of diastereomeric intermediates, after which enantioenriched material can be carried into protected amino acid synthesis. The indane-bearing side chain provides distinct steric and hydrophobic environments that can translate into measurable differences among diastereomeric forms during resolution strategies. Enantioenriched derivatives obtained from DL-2-Indanylglycine can then be used to build stereodefined peptide fragments and chiral peptidomimetic scaffolds for mechanistic and structure-function investigations.
4. Protected Amino Acid Chemistry
DL-2-Indanylglycine is applied in protected amino acid synthesis where N-protection and carboxyl activation enable controlled peptide coupling chemistry. The amino group can be converted into N-protected derivatives that withstand coupling conditions, while the carboxylic acid can be transformed into activated intermediates such as ester or acid-derivative forms for sequential assembly. The bulky indane substituent can improve stability of intermediates by reducing undesired side reactions and can influence reactivity during coupling, particularly in sterically demanding sequences. Protected DL-2-Indanylglycine derivatives therefore function as practical intermediates for generating amide-linked products, including peptide fragments and medicinal chemistry intermediates.
5. Process Chemistry Intermediates
DL-2-Indanylglycine is used in process chemistry intermediate preparation for fine chemical synthesis routes that require a robust amino acid-derived feedstock. The combination of a primary amine and carboxylic acid supports scalable transformations into activated carboxyl derivatives and amide-forming intermediates, which can be integrated into manufacturing workflows for peptide-like building blocks. The indane side chain provides a hydrophobic handle that can be carried through multi-step syntheses without losing the core amino acid functionality needed for downstream coupling. DL-2-Indanylglycine-derived intermediates can thus be employed to streamline production of substituted glycine analogs, peptidomimetic precursors, and other amino acid-based specialty chemicals.
6. Analytical Standards and Method Development
DL-2-Indanylglycine is applied in analytical research and method development where amino acid standards and derivatization-compatible analytes are needed for characterization of peptide synthesis mixtures. The amino acid functionality enables derivatization for chromatographic detection, including formation of detectable derivatives from the amine and carboxyl groups, supporting identity confirmation of incorporated residues. The indane-bearing structure provides a distinct hydrophobic signal profile that can aid separation from other amino acid components in complex reaction mixtures. DL-2-Indanylglycine can therefore serve as a reference material for monitoring coupling outcomes, evaluating stereochemical composition in DL workflows, and supporting quality control of amino acid derivative synthesis.
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