3-(2-Furyl)-DL-alanine is a DL (racemic) alanine derivative bearing a 2-furyl substituent on the side chain, classifying it as a non-proteinogenic, aromatic heterocycle-containing amino acid analogue. The molecule contains both an amino group and a carboxyl group characteristic of amino acids, with the heteroaromatic furan ring providing a distinct polar, π-rich side-chain functionality while the DL designation indicates a mixture of stereochemical forms at the α-carbon. It is used in peptide and amino acid analogue synthesis to introduce a furan-bearing side chain for structure-activity studies, chemical biology labeling strategies, and the preparation of more complex heteroaryl-substituted amino acid and peptide derivatives.
CAT No: CP21703
3-(2-Furyl)-DL-alanine is a DL (racemic) alanine derivative bearing a 2-furyl substituent at the beta position, providing an aromatic heterocycle that is routinely leveraged in medicinal chemistry and heteroaromatic SAR work. As an unprotected amino acid building block, it offers the free amino and carboxylic acid functionality needed for coupling into larger organic frameworks, including peptide-like scaffolds and non-peptidic amino acid analogs. Its heteroaryl side chain supports downstream derivatization and analytical characterization where a defined furan motif is required.
1. Peptidomimetic Building Blocks
3-(2-Furyl)-DL-alanine is used by peptide and peptidomimetic researchers as an amino acid building block to introduce a furan-containing side chain into constrained or analog scaffolds. Medicinal chemistry groups commonly incorporate this type of residue into short peptide-like sequences, backbone-modified analogs, or structure-activity relationship (SAR) libraries where the aromatic heterocycle is used to tune physicochemical properties and binding-site interactions. Because the material is supplied as a DL mixture, it is often selected for early-stage library synthesis and screening workflows where rapid access to analog diversity is prioritized over stereochemical uniformity.
2. Medicinal Chemistry SAR Intermediates
3-(2-Furyl)-DL-alanine serves as a practical intermediate for preparing heteroaryl-containing small molecules and amino acid-derived fragments used in SAR campaigns. Organic synthesis teams use the amino acid functionality as a handle for coupling, salt formation, or conversion into activated derivatives that can be merged with electrophiles or coupling partners to build larger medicinal chemistry targets. The 2-furyl motif is particularly useful when a heteroaromatic ring is required to probe electronic effects, hydrogen-bonding patterns, and aromatic/heteroaromatic recognition in structure-based or ligand-based design efforts.
3. Analytical Reference Derivatives
3-(2-Furyl)-DL-alanine is frequently employed in method development and reference standard preparation for analytical workflows that require a defined furan-bearing amino acid. Analytical chemistry laboratories use it to generate derivatized standards, calibration compounds, or internal-reference materials for chromatographic separation and mass spectrometric characterization of amino acid analogs and related reaction mixtures. The stable, well-defined heteroaryl side chain helps ensure consistent detection behavior when validating sample preparation steps, monitoring coupling reactions, or confirming the identity of furan-substituted intermediates during synthesis scale-up.
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