3-(3-Furyl)-D-alanine is a D-configured alanine derivative bearing a 3-furyl substituent on the side chain, classifying it as a non-proteinogenic aromatic heterocycle-containing amino acid. The molecule contains an amino group and a carboxyl group on the alanine backbone, with the heteroaromatic furan ring providing a distinct electron-rich, heteroatom-bearing side-chain functionality while maintaining the stereochemical definition implied by "D" in the name. It is used in peptide and structure-activity studies where incorporation of a furan-bearing amino acid analogue enables side-chain variation for chemical biology labeling, conjugation handle design, or analytical method development involving heteroaromatic motifs.
CAT No: CP21802
3-(3-Furyl)-D-alanine is a D-configured amino acid bearing a 3-furyl substituent on the side chain, providing an aromatic heterocycle that is commonly leveraged as a chemically distinctive building block in peptide and peptidomimetic design. Its heteroaromatic ring enables downstream structure-property studies and analytical traceability due to the strong, well-defined aromatic signature. Researchers use this non-proteinogenic amino acid to introduce a furan-containing residue into synthetic peptides and related scaffolds where stereochemical control and side-chain identity are important.
1. Peptide Building Block
3-(3-Furyl)-D-alanine is used by peptide chemists as a non-natural amino acid building block for incorporating a D-stereocenter and a 3-furyl side chain into custom peptides via standard peptide assembly workflows. The furan ring provides a clear structural handle for structure-activity relationship (SAR) studies, allowing medicinal chemistry teams to compare analogs that differ specifically at the side-chain aromatic motif while maintaining the same backbone stereochemical pattern. This residue is also valuable in generating peptides for conformational and stability investigations where alternating stereochemistry and side-chain electronics are used to probe how sequence context influences overall scaffold behavior.
2. Peptidomimetic SAR Studies
3-(3-Furyl)-D-alanine supports medicinal chemistry and chemical biology programs focused on peptidomimetic development, where non-natural amino acid substitutions are introduced to tune physicochemical properties and to map how heteroaromatic side chains contribute to binding-site interactions. The 3-furyl group offers a compact aromatic heterocycle that can participate in specific noncovalent interactions and provides a convenient motif for comparing closely related analog series. Teams developing constrained or stereochemically defined peptide-like molecules often select this building block to systematically evaluate the impact of D-amino acid incorporation alongside a furan-containing pharmacophore element.
3. Analytical Reference Standards
3-(3-Furyl)-D-alanine is frequently used as an analytical reference material for method development and characterization of synthetic mixtures, peptide hydrolysates, and labeled or derivatized analogs where the furan-containing side chain provides a distinctive chromatographic and spectrometric signature. Analytical chemists and process development groups use it to confirm identity and retention behavior for furan-bearing residues, and to support calibration or verification workflows when monitoring peptide composition by LC-MS or related techniques. The defined D-configuration and aromatic heterocycle help reduce ambiguity when distinguishing this residue from other common amino acid building blocks during impurity profiling and product characterization.
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