3-Amino-D-Phenylalanine contains the amino acid backbone with an amino group and a carboxyl group on the alpha carbon and a benzyl side chain, classifying it as a phenylalanine derivative in which the stereochemical form is specified as D. The molecule bears a primary amine at the alpha position and a carboxylic acid functionality suitable for salt formation or derivatization, while the aromatic phenyl side chain provides hydrophobic character and potential for π-π or aromatic interactions in peptide contexts. It is used as a stereodefined building block for preparing peptides and peptidomimetics containing D-phenylalanine residues, supporting structure-activity studies, conformational analysis, and analytical method development involving non-proteinogenic stereochemistry.
CAT No: CP10802
3-Amino-D-Phenylalanine is a D-configured phenylalanine analog bearing a free amino group at the 3-position of the aromatic ring. This non-proteinogenic amino acid is used as a chiral building block when aromatic substitution at the meta position is required for downstream peptide, peptidomimetic, or medicinal chemistry scaffolds. Its stereochemistry and aniline-type functionality make it a practical intermediate for installing aryl substituents and for preparing substituted aromatic amino acid derivatives used in structure-activity relationship studies and custom synthesis programs.
1. Peptidomimetic Building Blocks
3-Amino-D-Phenylalanine is used by medicinal chemistry and peptide-chemistry groups to construct peptidomimetic and substituted amino acid motifs where a meta-substituted phenyl ring is needed to probe binding-site interactions or to tune physicochemical properties. The D-configuration supports the preparation of stereochemically defined analogs for SAR work, including analog series where backbone stereochemistry is varied to evaluate conformational preferences. Researchers commonly incorporate this building block into solution-phase or solid-phase synthetic routes to generate non-natural peptide analogs and constrained aromatic systems for downstream biological characterization workflows.
2. Medicinal Chemistry Intermediates
3-Amino-D-Phenylalanine serves as a practical chiral intermediate for pharmaceutical intermediate development, particularly when an aniline-functionalized, D-amino acid framework is required to access substituted aromatic derivatives. Medicinal chemistry teams use the meta-amino functionality to enable selective downstream transformations that generate diverse aryl substitution patterns on a stereochemically controlled scaffold. This makes the compound valuable for preparing libraries of small-molecule fragments, aryl-containing side chains, and stereodefined intermediates that can be carried forward into lead-optimization chemistry.
3. Chiral SAR Analog Synthesis
3-Amino-D-Phenylalanine is frequently selected for stereochemically defined analog synthesis in structure-activity relationship programs where aromatic substitution and absolute configuration are both variables. Chemical biology and medicinal chemistry researchers use it to generate D-stereoisomer series and meta-substituted phenyl amino acid analogs that help disentangle the contributions of side-chain electronics and three-dimensional arrangement to observed structure-function trends. The combination of a defined D center and a reactive aromatic amino group supports systematic library construction for comparative studies across closely related analogs.
4. Aromatic Functionalization Studies
3-Amino-D-Phenylalanine is used in chemical biology and materials-oriented research when a meta-amino aromatic handle must be carried through as a functional group for further derivatization. The aromatic amine enables attachment of additional substituents or coupling partners during the build-out of complex scaffolds, including aryl-functionalized amino acid derivatives used as intermediates for downstream conjugation or scaffold elaboration. This approach is commonly used when researchers need a stereodefined aromatic amino acid core that can later be diversified without changing the chiral center.
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