Boc-D-Phenylalanine N-hydroxysuccinimide ester

Boc-D-Phenylalanine N-hydroxysuccinimide ester is a D-phenylalanine derivative bearing a Boc-protected amino group and an activated N-hydroxysuccinimide (NHS) ester for acyl transfer. This combination makes the compound a practical electrophilic amino acid building block for coupling reactions where rapid formation of amide bonds is required, while the D-configuration supports stereodefined incorporation into peptide segments and chiral chemical libraries. In research settings, it is commonly handled as a protected, activated intermediate that balances controlled reactivity with compatibility in peptide and bioconjugation workflows.

1. Peptide Coupling Building Block

Boc-D-Phenylalanine N-hydroxysuccinimide ester is used as an activated amino acid component in peptide synthesis workflows that require efficient amide-bond formation from a pre-formed nucleophile, such as an amino-functionalized resin linker, peptide fragment, or side-chain nucleophile. Peptide chemists select the NHS-activated form to promote fast coupling under mild conditions, while the Boc group provides orthogonal protection of the amino functionality during assembly. The D-phenylalanine stereochemistry is particularly valued when researchers aim to introduce conformational or proteolysis-resistance features into peptide analogs and chiral peptidomimetics, where stereochemical fidelity at the residue level matters.

2. Bioconjugation Amide Formation

Boc-D-Phenylalanine N-hydroxysuccinimide ester serves as an amino-acid-based acylating reagent for bioconjugation strategies that convert amine-bearing biomolecules (for example, lysine-containing proteins, peptides, or amine-functional polymers) into stable amide-linked conjugates. Chemical biology and biomaterials groups often rely on NHS ester chemistry to achieve controlled, high-yield coupling to primary amines, enabling attachment of a stereodefined amino acid moiety to create labeled constructs, affinity reagents, or functionalized macromolecules. The presence of the Boc-protected amino group helps maintain the reagent's identity as a defined acylating unit rather than an unprotected amino acid, supporting reproducible downstream processing in conjugate development.

3. Chiral Linker and Probe Synthesis

Boc-D-Phenylalanine N-hydroxysuccinimide ester is frequently incorporated into chiral linker architectures used in probe construction and analytical reagent development, where a phenylalanine-derived fragment is desirable for hydrophobic spacing, conformational bias, or stereochemical control. Researchers in chemical biology and materials science use the activated NHS ester to install the D-phenylalanine acyl group onto amine-functional scaffolds, including small-molecule handles, polymer backbones, and peptide-based tags. This approach supports the preparation of stereochemically defined intermediates for subsequent derivatization steps, such as further functional group transformations or assembly into larger probe systems, while the Boc protection helps preserve the intended coupling site during multistep synthesis.

4. Pharmaceutical Intermediate Development

Boc-D-Phenylalanine N-hydroxysuccinimide ester is also used as a stereodefined, activated acyl intermediate in pharmaceutical intermediate development where amide bond formation to an amine-containing partner is a key step. Process and R&D chemists value the NHS ester activation for its practical reactivity profile, enabling efficient conversion of an amino acid-derived acyl fragment into amide-linked intermediates used in the synthesis of peptidomimetic candidates and chiral building blocks. The D-configuration and Boc protection make it a useful option when maintaining stereochemical integrity and controlled functional group masking is required across a sequence of coupling and downstream transformations.

1. Uncarboxylated osteocalcin decreases insulin-stimulated glucose uptake without affecting insulin signaling and regulators of mitochondrial biogenesis in myotubes

2. Spatiotemporal delivery of nanoformulated liraglutide for cardiac regeneration after myocardial infarction

3. An interdomain binding site on HIV-1 Nef interacts with PACS-1 and PACS-2 on endosomes to down-regulate MHC-I

4. Myotropic activity and immunolocalization of selected neuropeptides of the burying beetle Nicrophorus vespilloides (Coleoptera: Silphidae)

5. High fat diet and GLP-1 drugs induce pancreatic injury in mice