(2R,3S)-3-Phenylisoserine is a non-proteinogenic, stereodefined amino acid derivative featuring a β-hydroxy amino acid framework with a phenyl-substituted side chain, distinguishing it from standard proteinogenic serine analogues. The molecule contains a primary amino group and a carboxyl group while bearing a secondary alcohol at the 3-position, and its (2R,3S) stereochemistry specifies the relative spatial arrangement of the α-carbon and the β-hydroxyl-bearing center. As a structurally modified amino acid, it is used in peptide and chemical biology research as a substrate analog for structure-activity studies, for preparing more complex amino acid derivatives, and for incorporation into synthetic peptide sequences where the hydroxyl-bearing phenyl side chain and defined stereochemistry affect conformational and interaction properties.
CAT No: CP26343
CAS No:136561-53-0
Synonyms/Alias:(2R,3S)-3-Phenylisoserine;136561-53-0;55325-53-6;(2R,3S)-3-amino-2-hydroxy-3-phenyl-propanoicacid;(2R,3S)-3-amino-2-hydroxy-3-phenylpropanoicacid;Benzenepropanoicacid,b-amino-a-hydroxy-,(aR,bS)-rel-;AC1ODTUJ;PubChem23579;SCHEMBL487425;(2R,3S)-3-Phenyl-Isoserine;CTK5A3414;MolPort-009-198-940;RZARFIRJROUVLM-JGVFFNPUSA-N;ZINC2567339;ANW-44799;SBB063517;AKOS006274499;AJ-41401;AK-33175;AN-31900;KB-01271;SC-20962;DB-063153;RT-019383;ST2414218
(2R,3S)-3-Phenylisoserine is a stereochemically defined, non-proteinogenic amino acid analog featuring a phenyl-substituted side chain and a primary amino acid functionality, making it a useful chiral building block for peptide and peptidomimetic design. Its defined (2R,3S) configuration supports structure-activity relationship studies where side-chain geometry and steric presentation are critical. Researchers also use this compound as a specialized intermediate for accessing conformationally informative amino acid derivatives in medicinal chemistry workflows.
1. Peptidomimetic Building Blocks
(2R,3S)-3-Phenylisoserine is used by medicinal chemistry and chemical biology teams to construct peptidomimetic scaffolds that probe how phenyl-bearing side-chain architecture influences binding, folding, or biological recognition. In practice, it serves as a stereodefined amino acid building block for preparing modified peptides and constrained analogs where the non-proteinogenic backbone element helps decouple structure from canonical proteinogenic residue behavior. This makes it particularly relevant for SAR campaigns that require consistent stereochemical input and reproducible side-chain presentation across analog series.
2. Chiral Synthesis Intermediate
(2R,3S)-3-Phenylisoserine is commonly employed in pharmaceutical intermediate development as a chiral starting material for downstream conversion into protected amino acid derivatives and other stereodefined intermediates used in custom synthesis. Process and R&D groups value the fixed stereochemical identity because it reduces ambiguity during later coupling or functional-group elaboration steps, supporting reliable scale-up of analog manufacturing. The phenyl-substituted side chain also provides a chemically robust handle for further derivatization strategies used to generate libraries of chiral intermediates for lead optimization.
3. Structure-Activity Relationship Studies
(2R,3S)-3-Phenylisoserine is applied in SAR and mechanistic chemistry studies where introducing a non-natural, stereodefined amino acid analog helps clarify the contribution of side-chain bulk and stereochemical orientation to observed structure-function trends. Researchers incorporate this residue into modified peptide-like constructs to compare how systematic changes around the phenyl-containing motif affect physicochemical properties and interaction patterns in assay systems. This application is especially relevant for teams building residue-scan or analog panels that require consistent stereochemical control rather than relying on racemic or undefined stereochemistry.
4. Analytical Reference Standards
(2R,3S)-3-Phenylisoserine is also used as an analytical reference material in method development and characterization workflows, including LC-MS or chiral analysis contexts where a defined stereoisomer is required for accurate identification and quantification. Analytical groups rely on stereochemically defined amino acid analogs to validate retention behavior, fragmentation patterns, or calibration strategies when monitoring synthetic intermediates or final analog mixtures. Its defined configuration and amino acid functionality make it a practical standard for confirming the identity of related chiral derivatives produced during research and development.
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