3-(3-Thienyl)-DL-alanine is a DL-form amino acid derivative belonging to the alanine family, featuring an alanine backbone bearing a 3-thienyl (thiophene) substituent on the side chain. It contains both an amino group and a carboxyl group, with the side chain presenting a heteroaromatic thiophene ring that can participate in hydrophobic and π-interactions during peptide or conjugate assembly. As a non-proteinogenic, aromatic side-chain amino acid analogue, it is used in peptide synthesis and structure-activity or binding studies where incorporation of a thiophene-bearing residue enables chemical probing, materials-related conjugation strategies, or analytical differentiation from standard amino acids.
CAT No: CP24301
3-(3-Thienyl)-DL-alanine is a DL-configured alanine derivative bearing a 3-thienyl aromatic side chain, providing a hydrophobic, heteroaromatic motif that is frequently leveraged in medicinal chemistry and structure-activity relationship studies. As a racemic amino acid building block, it is commonly used when stereochemical purity is not required at the discovery stage, and when the aromatic side chain is the primary contributor to physicochemical behavior. Its amino acid functionality makes it a practical precursor for peptide and peptidomimetic assembly, as well as for downstream conversion into activated intermediates for library synthesis.
1. Peptidomimetic Building Blocks
3-(3-Thienyl)-DL-alanine is used as an amino acid building block for the synthesis of peptidomimetics and constrained analogs where a thienyl side chain is incorporated to modulate hydrophobic surface area and aromatic interactions. Medicinal chemistry groups and contract research organizations often select this racemic alanine derivative to rapidly generate compound series that probe how heteroaromatic substitution influences potency, selectivity, and overall developability. The amino acid backbone supports straightforward incorporation into amide-linked scaffolds and related peptide-like structures, enabling efficient diversification during hit-to-lead optimization.
2. Structure-Activity Relationship Libraries
3-(3-Thienyl)-DL-alanine is frequently employed in parallel synthesis workflows to build SAR libraries containing thienyl-substituted alanine motifs. Small-molecule discovery teams use this reagent to systematically vary linker lengths, coupling patterns, and neighboring functional groups while keeping the heteroaromatic side chain constant. The DL form is particularly practical for early-stage library generation, where rapid throughput and broad chemical coverage are prioritized before any later-stage stereochemical refinement. This makes the compound a common choice for preparing analog sets used in biochemical screening campaigns and subsequent medicinal chemistry iteration.
3. Pharmaceutical Intermediate Development
3-(3-Thienyl)-DL-alanine serves as a useful intermediate for industrial and development chemistry programs that require a heteroaromatic alanine unit as a defined starting material. Process and synthesis teams use it to access thienyl-containing amide and related nitrogen-containing fragments that can be further elaborated into advanced intermediates for drug-discovery candidates and related specialty chemicals. The presence of both an amino acid handle and an aromatic thienyl group supports downstream functional group interconversions typical of intermediate manufacturing, enabling consistent feedstock for scalable synthesis routes.
4. Analytical Reference Material Synthesis
3-(3-Thienyl)-DL-alanine is also used to generate analytical standards and calibration compounds for method development in LC-MS and related characterization workflows. Analytical chemistry groups may incorporate this defined thienyl-alanine motif into reference materials used to monitor synthesis progress, verify intermediate identity, or support impurity profiling during process development. Because the reagent is a defined amino acid derivative with a distinct heteroaromatic signature, it can be leveraged to create structurally relevant standards that improve interpretability of chromatographic and mass spectrometric data for thienyl-containing series.
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