D-3-(3-benzofuranyl)-Alanine is a D-stereochemical, non-proteinogenic amino acid analogue featuring an alanine backbone substituted at the 3-position with a 3-benzofuranyl (benzofuran) aromatic side chain, rather than the methyl side chain of alanine. The molecule contains a free amino group and a free carboxyl group, and the benzofuran substituent provides a hydrophobic, π-rich aromatic functionality that can participate in stacking and other noncovalent interactions in peptide or small-molecule contexts. As a chemically defined amino acid building block, it is used in peptide synthesis and structure-activity or binding studies where incorporation of a benzofuran-bearing residue enables tuning of aromatic character, sterics, and physicochemical properties.
CAT No: CP20603
D-3-(3-benzofuranyl)-Alanine is a D-configured alanine derivative bearing a benzo-fused heteroaromatic substituent at the 3-position, creating a stereochemically defined chiral amino acid with an aromatic, electron-rich benzofuran ring. The molecule contains the amino acid functional set of a primary amine and a carboxylic acid, enabling formation of amide bonds for peptide coupling and allowing conversion to protected amino acid derivatives for controlled synthesis. The benzofuran side chain provides a rigid, π-rich aromatic handle that can participate in π-π interactions and can be chemically carried through peptide construction or later functionalization steps. The combination of a chiral amino acid core and a heteroaryl substituent makes the compound suitable as a stereodefined intermediate for peptide building block preparation, chiral SAR probe synthesis, and downstream heteroaromatic-containing analog generation.
1. Peptide Synthesis
D-3-(3-benzofuranyl)-Alanine serves as a direct amino acid component for peptide building block preparation in solid-phase or solution-phase assembly, where the carboxylic acid and amino group enable amide bond formation. The D-stereocenter on the alanine backbone supports incorporation of a defined stereochemical motif into peptides, while the benzofuran side chain remains stable under typical peptide coupling conditions and can be carried into the final sequence. Use of N- and C-protection strategies, such as temporary N-protection and carboxyl activation, can be applied to control chemoselective coupling and to minimize side reactions from the heteroaryl-containing side chain. The resulting benzofuran-containing peptides and peptide fragments can function as research reagents for studying sequence effects, conformational preferences, and side-chain recognition in amino acid chemistry and peptide science.
2. Chiral SAR Studies
D-3-(3-benzofuranyl)-Alanine supports structure-activity relationship studies by providing a stereodefined D-amino acid variant with a benzofuran aromatic pharmacophore-like element. The heteroaryl substituent introduces polarity and aromatic surface area that can be used to probe binding interactions, while the alanine backbone constrains the spatial presentation of the side chain relative to the stereocenter. Protection-group planning for peptide or amide formation allows the compound to be incorporated into analog libraries as a consistent chiral unit, enabling comparative evaluation of stereochemical and side-chain effects. Downstream derivatives prepared from this intermediate, including amide-linked fragments and peptide analogs, can be used to generate SAR-relevant scaffolds in medicinal chemistry workflows.
3. Chemical Biology Probes
D-3-(3-benzofuranyl)-Alanine can be employed in chemical biology research as a chiral amino acid handle for building labeled or functionalized biomolecular probes. The benzofuran ring can be retained as a recognition element while the amino acid core enables conversion into amide-linked conjugates, including bioconjugation-ready intermediates after appropriate protection and activation. Side-chain functionalization may be designed through post-coupling derivatization strategies that preserve the D-configuration at the backbone during conjugate assembly. The resulting heteroaryl-containing conjugates can be used as molecular tools for investigating biomolecular interactions, mapping binding preferences, and generating structurally defined probe sets from amino acid chemistry.
4. Protected Amino Acid Chemistry
D-3-(3-benzofuranyl)-Alanine is suitable for conversion into protected amino acid derivatives that support controlled peptide coupling and selective deprotection logic. The presence of both a primary amine and a carboxylic acid enables N-protection to suppress undesired reactions during side-chain or backbone modifications, while carboxyl activation or esterification can prepare the molecule for stepwise synthesis. The D-chiral center provides stereochemical integrity through protection and coupling steps, which is critical when generating stereochemically consistent peptide building blocks and chiral intermediates. Downstream, protected derivatives can be used to manufacture benzofuran-bearing peptide fragments, chiral amide intermediates, and process-compatible intermediates for fine chemical synthesis.
5. Process Chemistry Intermediate
D-3-(3-benzofuranyl)-Alanine can function as a chiral intermediate in process chemistry for manufacturing heteroaryl-containing amino acid derivatives and peptide-related intermediates. The stable amino acid functionality allows integration into scalable protection, activation, and coupling sequences, while the benzofuran side chain can be carried through as a chemically robust motif that does not require disruptive transformations during peptide assembly. Stereochemical control is inherently supported by the D-configuration, enabling consistent feedstock behavior when producing peptide building blocks, amide fragments, or chiral SAR materials. The compound's defined structure supports downstream conversion into activated forms for chemical manufacturing routes targeting benzofuran-substituted analogs and amino acid-based specialty chemicals.
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