L-Phenylglycine is a natural amino acid analogue classified as an α-amino acid, featuring an α-amino group and a carboxyl group attached to a side chain bearing a benzyl-like phenyl substituent. The molecule is present as the L-stereochemical form as indicated by its name and contains a hydrophobic aromatic side chain that can influence peptide conformation and intermolecular interactions. L-Phenylglycine is used in peptide chemistry and structure-activity studies as a substrate or building block for incorporating a phenylglycine residue into peptides, enabling evaluation of how aromatic side-chain placement affects binding, stability, and physicochemical properties.
CAT No: CP09702
CAS No:2935-35-5
Synonyms/Alias:2935-35-5;(S)-2-Amino-2-phenylaceticacid;L-Phenylglycine;H-Phg-Oh;L-2-Phenylglycine;L-(+)-alpha-Phenylglycine;(S)-phenylglycine;Phenylglycine;(2S)-amino(phenyl)aceticacid;(S)-(+)-2-Phenylglycine;L-(+)-alpha-Aminophenylaceticacid;L-(+)-2-Phenylglycine;L-(+)-a-Phenylglycine;(2S)-2-amino-2-phenylaceticacid;L(+)-alpha-Phenylglycine;CHEMBL378605;DL-Phenylglycine;CHEBI:439819;S-(+)-alpha-Aminophenylaceticacid;(S)-AMINO-PHENYL-ACETICACID;(alphaS)-alpha-aminobenzeneaceticacid;(S)-(+)-alpha-AminophenylaceticAcid;NSC206293;69-91-0;L-alpha-Phenylglycine
L-Phenylglycine is an L-configured amino acid analog featuring a stereogenic center at the alpha carbon and a benzyl-substituted side chain (phenylmethyl group), giving it a chiral, aromatic-rich scaffold. The molecule contains a primary amino group and a carboxylic acid functionality, which together support salt formation and controlled reactivity in peptide coupling and derivatization chemistry. The benzylic position adjacent to the aromatic ring can participate in stereochemically relevant transformations, while the aromatic ring enables π-interactions that are often leveraged in molecular recognition and SAR-oriented design. As an amino acid building block and chiral intermediate, L-Phenylglycine can be converted into protected amino acid derivatives or activated carboxylic acid forms for downstream synthesis of peptidomimetics, constrained analogs, and chiral intermediates for fine chemical production.
1. Peptide Synthesis
L-Phenylglycine is incorporated into peptide coupling workflows as an L-amino acid building block where its carboxylic acid and amino group enable amide bond formation under standard peptide coupling chemistries. The benzylic phenylmethyl side chain provides a hydrophobic, aromatic substituent that can modulate local conformational preferences in peptide chains and peptidomimetic scaffolds. Protection of the amino group and activation or protection of the carboxyl group can be used to manage chemoselectivity during sequential assembly, including strategies compatible with solid-phase or solution-phase synthesis. The resulting phenylglycine-containing peptides and analogs serve as research materials for structure-activity relationship studies and for mapping how aromatic side-chain placement affects binding and stability.
2. Chiral Building Block Development
L-Phenylglycine functions as a chiral amino acid intermediate for stereoselective synthesis of enantiopure fine chemicals and medicinal chemistry fragments. The L-configuration at the alpha carbon provides a stereochemical handle that can be retained through conversion into N-protected derivatives, activated esters, or carboxyl-activated coupling partners. The phenylmethyl side chain can be further elaborated via functional group interconversions that preserve chirality, supporting access to benzylic alcohol, halide, or substituted aromatic intermediates used in downstream scaffold construction. Chiral derivatization of L-Phenylglycine can also support analytical method development where enantiomeric discrimination and stereochemical assignment are required.
3. Peptidomimetics And SAR
L-Phenylglycine is suitable for peptidomimetic construction because its aromatic side chain can reproduce key hydrophobic contacts while the alpha-amino acid backbone supports conformational tuning relative to glycine or phenylalanine analogs. The amino and carboxyl groups enable iterative derivatization into amide-linked motifs, while side-chain functionalization can be used to probe steric and electronic effects on molecular recognition. Protecting-group strategies for the amino functionality and controlled activation of the carboxyl group facilitate incorporation into constrained or backbone-modified analog series used in structure-activity relationship studies. Phenylglycine-containing analogs can be employed as biochemical research tools to examine how aromatic substitution patterns influence binding mode and structure-dependent properties.
4. Chemical Biology Probes
L-Phenylglycine can be utilized in chemical biology research to generate amino acid-based probes and conjugation-ready intermediates that retain a stereodefined backbone. The primary amino functionality can be converted into N-protected forms and subsequently into reactive handles for downstream conjugation, while the carboxyl group can be transformed into activated esters or amide-forming derivatives for attachment to carriers or targeting scaffolds. The aromatic phenylmethyl side chain can support fluorescence or affinity tagging strategies when paired with appropriate labeling reagents, enabling tracking of biomolecular interactions in experimental workflows. Phenylglycine-derived conjugates also serve as intermediates for preparing biomolecule-modified materials where controlled incorporation of an L-amino acid motif is required.
5. Pharmaceutical Intermediate Preparation
L-Phenylglycine is applied as a chiral intermediate in pharmaceutical and specialty chemical manufacturing routes where enantiopure amino acid fragments are needed for building complex molecules. The amino acid's functional groups allow conversion into protected amino acid derivatives and activated carboxylic acid intermediates that participate in stepwise assembly of drug-like structures and heteroatom-containing motifs. Aromatic side-chain chemistry can be leveraged for introducing phenylmethyl substituents into larger frameworks, supporting process chemistry that relies on predictable protection/deprotection cycles and chemoselective coupling steps. Downstream use includes preparation of enantiopure intermediates for fine chemical synthesis and the generation of stereodefined building blocks for iterative medicinal chemistry campaigns.
6. Analytical Research Standards
L-Phenylglycine can serve in analytical research as a reference compound for method development and stereochemical verification of amino acid derivatives. The defined L-configuration and aromatic side chain facilitate chromatographic separation and can support calibration of assays targeting amino acid building blocks, protected amino acid derivatives, or peptide hydrolysates containing phenylglycine units. Derivatization of the amino and/or carboxyl functionality enables formation of detectable derivatives for LC, GC, or capillary electrophoresis workflows where functional group-specific detection is advantageous. Phenylglycine-containing standards also support impurity profiling and identity confirmation in quality-relevant synthetic intermediate characterization within amino acid and peptide chemistry pipelines.
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