Fmoc-3-(3-benzothienyl)-L-alanine is an Fmoc-protected amino acid derivative in which the alanine backbone bears a 3-(3-benzothienyl) substituted side chain, corresponding to a non-natural, aromatic, sulfur-containing amino acid analog used for peptide construction. The molecule contains a free carboxyl group and an Fmoc carbamate on the amino functionality, with the side chain presenting a benzothiophene aromatic system that can participate in hydrophobic and π-interactions while the stereocenter is specified as L by the product name. In synthesis, the Fmoc-protected format supports stepwise incorporation of this residue into peptides or peptide-like intermediates under controlled deprotection conditions, and the benzothiophene handle can be used in structure-activity studies, labeling strategies, or materials-oriented conjugation workflows where an aromatic, heteroaromatic side chain is required.
CAT No: CP20704
Fmoc-3-(3-benzothienyl)-L-alanine is an Fmoc-protected L-alanine derivative bearing a chiral alpha carbon and a thioether-containing benzothiophene side chain at the 3-position relative to the backbone. The molecule contains an N-(9H-fluoren-9-ylmethoxycarbonyl) carbamate that suppresses amine reactivity during peptide assembly while enabling orthogonal deprotection under standard base conditions. The benzothienyl substituent provides a rigid, π-rich aromatic surface that can participate in hydrophobic contacts and noncovalent recognition, while the carboxylate functionality is present as the amino-acid acid form suitable for peptide coupling chemistry. The combination of stereodefined amino acid geometry, protected amine, and aromatic heterocycle makes it a practical chiral building block for constructing substituted peptidomimetics and for preparing downstream intermediates in fine chemical synthesis.
1. Peptide Synthesis
Fmoc-3-(3-benzothienyl)-L-alanine is used in solid-phase and solution-phase peptide synthesis where the Fmoc carbamate protects the N-terminus during iterative coupling cycles. The L-alanine stereocenter and the side-chain benzothienyl aromatic heterocycle influence coupling outcomes and conformational preferences of the growing chain, supporting the construction of sequence-defined peptides and peptide fragments. The free carboxylic acid functionality enables amide bond formation with activated coupling reagents, allowing incorporation as a single residue or as part of longer heteroaromatic-containing segments. The resulting peptidic products can serve as research-grade scaffolds for studying aromatic side-chain effects on folding, binding, and stability, linking amino acid chemistry to peptide science.
2. Peptidomimetics And SAR
Fmoc-3-(3-benzothienyl)-L-alanine is applied in peptidomimetic construction and structure-activity relationship studies where the benzothiophene-like side chain provides a defined hydrophobic and π-interaction motif. The protected amino acid format supports controlled introduction of this aromatic heterocycle into analog series while maintaining the L-configuration at the alpha carbon. Side-chain incorporation via peptide coupling chemistry can be paired with subsequent functional group transformations on the aromatic system or backbone to generate analogs with altered electronic character and steric profile. The compound can therefore function as a chiral intermediate for SAR-focused library synthesis, enabling systematic evaluation of how heteroaromatic substitution patterns affect molecular recognition.
3. Chemical Biology Probes
Fmoc-3-(3-benzothienyl)-L-alanine is suitable for chemical biology research where aromatic heterocycles are leveraged for labeling, affinity capture, and probe design. The Fmoc-protected amine supports stepwise assembly of probe precursors into peptides or peptide-like constructs that retain stereochemical fidelity. The benzothienyl moiety can be used as a recognition handle within conjugates, while the amino acid backbone provides a chemically addressable platform for later deprotection and derivatization into bioconjugation-ready scaffolds. Downstream products derived from this residue can be employed as molecular probes for studying biomolecular interactions, enabling amino acid derivatization strategies that connect synthetic peptide chemistry to biochemical investigation.
4. Bioconjugation Linkers
Fmoc-3-(3-benzothienyl)-L-alanine is utilized in bioconjugation chemistry as a protected amino acid building block for preparing linker-containing conjugates. The Fmoc group enables orthogonal protection during synthesis, allowing selective exposure of the amine after assembly for conjugation to electrophiles or activated carboxylic acid partners. The presence of a rigid benzothienyl aromatic side chain can improve stability of conjugates and can serve as a hydrophobic anchor that modulates solubility and binding to target surfaces. The resulting conjugation-ready intermediates support downstream formation of labeled biomolecules and engineered constructs used in applied biochemical research and analytical workflows.
5. Pharmaceutical Intermediate Preparation
Fmoc-3-(3-benzothienyl)-L-alanine is relevant to pharmaceutical intermediate preparation and fine chemical synthesis where stereodefined, protected amino acids are required for scalable route design. The Fmoc-protected carbamate and carboxylic acid functionality align with common peptide-coupling manufacturing steps, facilitating incorporation into larger fragments that later undergo deprotection and conversion to final amide-containing intermediates. The benzothienyl heteroaromatic side chain can serve as a structural element in drug-like scaffolds, making this residue a practical chiral building block for heteroaromatic-containing series. The compound's compatibility with protected amino acid chemistry supports controlled downstream transformations toward API-adjacent intermediates and process-ready molecular fragments.
6. Process Chemistry and Specialty Synthesis
Fmoc-3-(3-benzothienyl)-L-alanine is suitable for process chemistry and specialty chemical production where reproducible handling of chiral protected amino acids is required. The Fmoc group provides a stable, isolable N-protecting strategy that can be removed cleanly to reveal the nucleophilic amine for subsequent coupling or conjugation steps in a manufacturing sequence. The benzothienyl side chain contributes defined aromatic character that can be carried through synthesis as a robust moiety without requiring additional protecting-group manipulation for the heteroaromatic core. The compound can be employed as a chiral intermediate for producing heteroaromatic peptide building blocks, peptidomimetic precursors, and other amino-acid-derived intermediates used in industrial chemical manufacturing and applied synthetic methodology.
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4. SERS spectrum of the peptide thymosin‐β4 obtained with Ag nanorod substrate
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