3-(3-Furyl)-DL-alanine is a DL (racemic) amino acid derivative featuring an alanine backbone bearing a 3-furyl substituent on the side chain, classifying it as a non-proteinogenic aromatic heterocycle-substituted amino acid. The molecule contains a free amino group and a free carboxyl group and presents the side chain with a furan ring that can participate in π-π and heteroatom interactions while remaining chemically distinct from standard aliphatic residues. As a substituted amino acid, it is used in peptide and amino acid derivative synthesis and in structure-activity or chemical biology studies where a furan-bearing side chain provides a stable aromatic handle for conjugation, labeling, or analytical method development.
CAT No: CP21803
3-(3-Furyl)-DL-alanine is a DL (racemic) amino acid bearing a 3-furyl side chain, combining an amino acid backbone with a heteroaromatic functional group that is stable under typical peptide-coupling and organic synthesis conditions. This structure makes it useful as a heteroaryl-containing building block for medicinal chemistry and heteroaryl-substituted peptide or peptidomimetic analog preparation, where the furan ring can contribute to binding-site interactions and physicochemical tuning. As a racemate, it is commonly selected for structure-activity relationship studies and intermediate synthesis where stereochemical resolution is addressed downstream if required.
1. Peptidomimetic Building Block
3-(3-Furyl)-DL-alanine is used by peptide chemistry and medicinal chemistry teams to introduce a furan-containing side chain into peptidomimetic scaffolds and analog libraries. Its amino acid functionality supports incorporation into amide-linked structures during custom synthesis workflows, enabling researchers to probe how heteroaromatic substitution affects conformation, receptor/target engagement patterns, and overall molecular properties. Because the material is supplied as a DL mixture, it is frequently chosen for early-stage structure-activity relationship (SAR) work where rapid access to heteroaryl analogs is prioritized before any stereochemical optimization.
2. Medicinal Chemistry Intermediate
3-(3-Furyl)-DL-alanine serves as a practical intermediate for constructing heteroaryl-substituted small molecules and amino acid-derived fragments used in drug discovery chemistry. The 3-furyl side chain provides a chemically distinctive motif that can be carried through to downstream transformations, including derivatization to generate substituted heteroaryl pharmacophores or to build constrained motifs that mimic amino acid side-chain presentation. Medicinal chemistry groups often select this building block when they need a readily handled amino acid precursor that already contains the key heteroaromatic element, streamlining the assembly of furan-bearing compound series.
3. Heteroaryl SAR Library Synthesis
3-(3-Furyl)-DL-alanine is widely used for generating heteroaryl-substituted compound libraries in academic and industrial screening support settings. The racemic nature allows efficient parallel synthesis of analogs without requiring immediate chiral resolution, which is advantageous when compound activity trends are being established across multiple side-chain variants. Researchers leverage the furan ring to explore electronic and hydrogen-bonding contributions from the heteroaromatic group while using the amino acid backbone as a modular handle for assembling diverse derivatives, including amide and related linkages common to SAR campaigns.
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