3-(3-Furyl)-L-alanine is an L-alanine derivative in which the side chain bears a 3-furyl (furan-3-yl) substituent, making it a nonstandard amino acid suitable for peptide and structure-activity studies. The molecule contains both an amino group and a carboxyl group characteristic of amino acids, with the furan ring providing an aromatic heterocycle that can participate in π-π interactions and serve as a chemical handle for conjugation or analytical detection. In synthesis, it is used as a defined building block for incorporating the 3-furyl side chain into peptides or amino acid derivatives, supporting studies that compare aromatic heterocycle substitution patterns in biomolecular constructs.
CAT No: CP21801
3-(3-Furyl)-L-alanine is an L-amino acid featuring a side chain terminated with a 3-furyl (furan) aromatic ring, providing a compact heteroaromatic motif that is frequently leveraged in medicinal chemistry and structure-activity relationship (SAR) studies. As a stereodefined amino acid, it serves as a chemically defined building block for preparing peptidomimetics and amino-acid-derived scaffolds where the furan ring contributes distinct electronic and hydrogen-bonding characteristics. In research workflows, its defined chirality and heteroaromatic functionality make it a practical precursor for assembling bioactive analogs and for generating analytical standards that retain the intact amino-acid framework.
1. Peptidomimetic Building Blocks
3-(3-Furyl)-L-alanine is used by medicinal chemistry groups to construct peptidomimetic and amino-acid-derived scaffolds that incorporate a heteroaromatic furan ring at a defined stereochemical position. The furan side chain offers a convenient handle for downstream derivatization into substituted analogs used in SAR campaigns, while the amino acid backbone enables straightforward conversion into coupling-ready intermediates for assembling short peptide-like structures. This application is especially common in lead optimization efforts where researchers need a consistent, structurally characterized building block to probe how heteroaromatic electronics and geometry influence binding interactions and overall scaffold behavior.
2. Peptide Synthesis Analog Development
3-(3-Furyl)-L-alanine is selected for custom peptide and peptide-analog synthesis workflows where incorporation of a furyl-containing residue is required to evaluate sequence-dependent effects in chemical biology and protein chemistry studies. Because the compound is an L-amino acid with a defined side-chain aromatic group, it can be used to prepare residue-containing fragments or analogs that are subsequently assembled into longer constructs by standard peptide-building strategies used in research settings. Teams developing modified peptides for binding studies, receptor/ligand interaction mapping, or structure-function experiments often prefer such defined amino-acid inputs to ensure the heteroaromatic moiety is introduced with controlled stereochemistry and positional integrity.
3. SAR and Heteroaromatic Intermediate Synthesis
3-(3-Furyl)-L-alanine is widely used in pharmaceutical intermediate development to access heteroaromatic amino-acid-derived intermediates for analog libraries. The 3-furyl side chain provides a chemically informative motif that can be retained or transformed during synthesis of substituted derivatives, supporting parallel synthesis approaches where multiple analogs must share a common stereochemical core. Process and development chemists value the compound as a starting point for making structurally consistent intermediates that feed into later stages of medicinal chemistry programs, including the preparation of furan-substituted amino-acid derivatives used to explore chemical space around heteroaromatic pharmacophores.
4. Analytical Standard and Method Development
3-(3-Furyl)-L-alanine is employed as a reference material in analytical method development and characterization workflows that require an authentic heteroaromatic amino-acid standard. Researchers use it to support LC-MS and related analytical setups when monitoring amino-acid-containing intermediates, verifying identity during synthesis, or calibrating quantitation approaches for furyl-substituted building blocks. In quality control and research analytics, the intact L-amino-acid structure helps ensure that retention time, mass spectral features, and derivatization behavior are anchored to a known compound rather than inferred from structurally related analogs.
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