L-3-(3-benzofuranyl)-Alanine is an L-configured, non-proteinogenic amino acid derivative of alanine bearing a 3-benzofuranyl substituent on the side chain, classifying it as an aromatic, heteroaryl-substituted amino acid. The molecule contains a free amino group and a free carboxyl group characteristic of amino acids, with the benzofuran ring providing a planar, hydrophobic aromatic surface and heteroatom-containing functionality that can participate in noncovalent interactions. In peptide chemistry and structure-activity studies, it is used as a building block for incorporating the benzofuranyl-bearing residue into peptides or peptide mimetics, and it can also serve as a substrate or reference compound in analytical method development for amino acid derivatives.
CAT No: CP20602
L-3-(3-benzofuranyl)-Alanine is an L-configured amino acid bearing a benzofuran-substituted side chain at the β-position, combining a stereogenic α-carbon with a heteroaromatic ring system. The molecule contains a primary amino functionality and a carboxylic acid group (or, depending on the supplied form, a corresponding protected/activated derivative), enabling standard amino acid coupling chemistry while maintaining the chiral information required for enantiospecific synthesis. The benzofuran moiety introduces aromatic π-systems and heteroatom sites that can participate in π-π interactions and electrophile/oxidant compatibility during downstream derivatization. As a chiral amino acid intermediate, it can be incorporated into peptide-like scaffolds or converted into protected amino acid derivatives for controlled N- and C-terminal manipulation.
1. Peptide Synthesis
L-3-(3-benzofuranyl)-Alanine is used in peptide building block preparation where the L-α-amino acid framework supports amide bond formation under peptide coupling conditions. The side-chain benzofuran group remains chemically defined during N-protection and C-activation strategies, allowing incorporation into linear peptides and peptide fragments with preserved stereochemistry at the α-carbon. The amino and carboxyl functionalities can be orthogonally protected to enable sequential coupling, supporting synthesis of benzo-furan-containing analogs for structure-activity relationship studies. Downstream, the resulting peptide intermediates can be deprotected to yield target sequences or used as protected fragments in iterative peptide assembly workflows.
2. Peptidomimetics And SAR
L-3-(3-benzofuranyl)-Alanine is applied in peptidomimetic and SAR-focused medicinal chemistry programs that require heteroaromatic side-chain presentation at a defined chiral center. The benzofuran substituent provides a rigid, planar aromatic element that can modulate conformational preferences when embedded into peptide analogs or constrained scaffolds. Protected amino acid derivative forms of L-3-(3-benzofuranyl)-Alanine can be incorporated into turn-mimetic or side-chain-functionalized frameworks, enabling systematic variation of linker length and neighboring residues while maintaining stereochemical control. The benzofuran-bearing residue can also serve as a handle for later functional group transformation, supporting generation of analog libraries for binding and selectivity mapping.
3. Chemical Biology Probes
L-3-(3-benzofuranyl)-Alanine is suitable for chemical biology research where amino acid side-chain heteroaromatics can be used to construct labeled or affinity-tagged biomolecule fragments. The amino acid backbone enables conjugation strategies through N-protection/deprotection and carboxyl activation, while the benzofuran ring can function as a stable aromatic motif for probe design and molecular recognition. Derivatization of the benzofuran-containing residue into electrophile-reactive or clickable forms can support incorporation into peptides, peptidic ligands, or protein-binding constructs. Resulting conjugation-ready intermediates can be used to generate biochemical research tools for studying biomolecular interactions at the level of defined residue placement.
4. Protected Amino Acid Chemistry
L-3-(3-benzofuranyl)-Alanine is used as a chiral starting material for producing N-protected and/or C-activated amino acid derivatives that are compatible with peptide coupling and orthogonal deprotection schemes. The presence of the α-amino and carboxyl groups enables conversion to common protected amino acid formats, supporting controlled reactivity during stepwise synthesis of protected peptide segments. The benzofuran side chain is chemically stable under typical protection and activation conditions, permitting iterative assembly without altering the heteroaromatic motif. Downstream, protected derivatives derived from this amino acid can serve as processable intermediates for fine chemical synthesis and for manufacturing routes that require reproducible chiral building blocks.
5. Analytical Standards And Method Development
L-3-(3-benzofuranyl)-Alanine is employed in analytical research as a reference compound for method development involving amino acid profiling, chiral analysis, and peptide hydrolysate characterization. The defined L-configuration and benzofuran-containing side chain produce distinct chromatographic and spectrometric signatures that can support identification and quantitation of residues in complex matrices. The amino acid's functional groups enable derivatization workflows, such as conversion to detectable derivatives for LC-MS or GC-compatible analysis, while the benzofuran ring can improve signal detectability in aromatic-sensitive detection modes. Analytical standards prepared from this compound can be used to validate sample preparation and to monitor incorporation of benzofuran-bearing residues in peptide synthesis and downstream processing.
6. Pharmaceutical Intermediate Preparation
L-3-(3-benzofuranyl)-Alanine is relevant to pharmaceutical intermediate preparation where chiral, heteroaromatic amino acid residues are incorporated into drug-like scaffolds and synthetic intermediates. The stereogenic α-carbon and protected amino acid chemistry enable predictable routing into amide-forming steps, supporting synthesis of peptide-like fragments, non-peptidic analogs, and constrained side-chain variants. The benzofuran moiety can participate in later functional group transformations or serve as a stable aromatic core within larger molecules, aligning with process chemistry needs for chemically robust intermediates. Industrially, this amino acid can be used to design scalable synthetic sequences for generating chiral building blocks used in specialty chemical production and fine chemical manufacturing.
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