3-(3-Thienyl)-D-alanine is a non-proteinogenic, aromatic amino acid derivative featuring a D-configured α-amino acid backbone bearing a 3-thienyl substituent on the side chain, along with a free amino group and a free carboxyl group. The heteroaromatic thiophene ring provides a conjugated, sulfur-containing side-chain functionality that can participate in hydrophobic and π-interaction patterns while the α-amino and α-carboxyl groups enable standard amino-acid chemistry such as salt formation and peptide-bond formation. It is used in peptide synthesis and structure-activity or chemical biology studies where incorporation of a thiophene-bearing, stereodefined residue supports the preparation of modified peptides and analytical standards.
CAT No: CP24303
3-(3-Thienyl)-D-alanine is a D-configured amino acid bearing a 3-thienyl aromatic side chain, providing a rigid, heteroaromatic motif that is frequently leveraged in structure-activity relationship studies and non-natural amino acid incorporation. Its primary amino and carboxylic acid functionality make it a practical building block for peptide and peptidomimetic synthesis, while the thienyl group supports downstream derivatization and analytical discrimination in chemical biology and medicinal chemistry workflows. Researchers typically select this stereodefined, heteroaromatic amino acid when they need consistent side-chain electronics and steric presentation in designed analogs.
1. Peptide And Peptidomimetic Synthesis
3-(3-Thienyl)-D-alanine is used as a non-proteinogenic amino acid building block for custom peptide synthesis and peptidomimetic development, particularly when a D-amino acid configuration is desired to tune backbone stereochemistry and protease resistance trends in designed analogs. Medicinal chemistry groups incorporate the 3-thienyl side chain to introduce aromatic heterocycle character into short peptides, constrained peptidomimetics, and SAR libraries, where the thienyl ring can influence conformation and physicochemical properties. In practice, this amino acid is supplied for downstream coupling into protected peptide intermediates or for segment construction in workflows that require a defined D stereocenter and a heteroaromatic side chain.
2. Medicinal Chemistry SAR Building Block
3-(3-Thienyl)-D-alanine is widely used in structure-activity relationship (SAR) campaigns as a stereodefined heteroaromatic amino acid component for analog synthesis. Pharmaceutical research teams and academic medicinal chemistry laboratories employ it to systematically vary aromatic heterocycle identity and stereochemistry within peptide-like scaffolds, enabling comparative evaluation of structure-property relationships such as lipophilicity and aromatic electronic effects. The thienyl substituent provides a chemically distinct handle compared with phenyl analogs, supporting rational design of binding-site interactions and improving interpretability of structure changes across a series of D-amino acid-containing compounds.
3. Chemical Biology Probe And Tag Synthesis
3-(3-Thienyl)-D-alanine can be used to prepare chemical biology reagents where an aromatic heterocycle is required as a recognition element, scaffold, or analytical tag within a peptide or small-molecule conjugate. Researchers use the D-alanine backbone to introduce stereochemical control into labeled constructs, while the 3-thienyl side chain offers a stable aromatic motif that can be retained during subsequent conjugation steps or used as a differentiating structural element in complex mixtures. This makes the compound useful for designing probe precursors for affinity-based studies, labeling strategies, and mechanistic experiments where consistent heteroaromatic presentation improves interpretability of downstream analytical readouts.
4. Analytical Reference For Heteroaromatic Amino Acid Studies
3-(3-Thienyl)-D-alanine is also used as an analytical reference standard and synthetic benchmark in method development and characterization of heteroaromatic amino acid derivatives. Analytical chemistry teams employ it to verify identity and retention behavior of thienyl-containing amino acid building blocks and to support LC-MS workflows that distinguish D-configured, heteroaromatic side chains from closely related analogs. Because the compound contains a defined D stereocenter and a characteristic 3-thienyl moiety, it is particularly useful when developing separation methods, confirming derivatization outcomes, or establishing calibration materials for quantitative tracking of thienyl amino acid incorporation into larger peptide-like systems.
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3. SERS spectrum of the peptide thymosin‐β4 obtained with Ag nanorod substrate
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