Fmoc-β-(3-thienyl)-L-alanine
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Fmoc-β-(3-thienyl)-L-alanine

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Category
Fmoc-Amino Acids
Catalog number
BAT-005542
CAS number
186320-06-9
Molecular Formula
C22H19NO4S
Molecular Weight
393.40
Fmoc-β-(3-thienyl)-L-alanine
IUPAC Name
(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-thiophen-3-ylpropanoic acid
Synonyms
Fmoc-3-L-Ala(3-thienyl)-OH; (S)-2-(Fmoc-amino)-3-(3-thienyl)propionic acid
Appearance
Pale white or white solid
Purity
≥ 98% (Chiral HPLC, HPLC)
Density
1.343g/cm3
Melting Point
176-182 °C
Storage
Store at 2-8°C
InChI
InChI=1S/C22H19NO4S/c24-21(25)20(11-14-9-10-28-13-14)23-22(26)27-12-19-17-7-3-1-5-15(17)16-6-2-4-8-18(16)19/h1-10,13,19-20H,11-12H2,(H,23,26)(H,24,25)/t20-/m0/s1
InChI Key
LSBZJMRHROCYGY-FQEVSTJZSA-N
Canonical SMILES
C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)NC(CC4=CSC=C4)C(=O)O

Fmoc-β-(3-thienyl)-L-alanine, a protected amino acid employed in peptide synthesis and diverse bioscience applications, offers a myriad of possibilities. Here are the key applications presented with heightened perplexity and burstiness:

Peptide Synthesis: Serving as a fundamental element in the solid-phase assembly of peptides, Fmoc-β-(3-thienyl)-L-alanine brings a distinctive structure to the table. This structure facilitates the integration of thiophene moieties into peptides, augmenting binding capabilities or introducing fresh functionalities. This attribute proves invaluable in crafting peptide-based therapeutics and materials boasting specialized chemical characteristics.

Drug Development: Within the realm of pharmaceutical exploration, Fmoc-β-(3-thienyl)-L-alanine finds utility in the manipulation of peptide sequences for potential drug discovery endeavors. The incorporation of thienyl groups can exert influence over the pharmacokinetic and pharmacodynamic attributes of peptides. Researchers leverage this amino acid to engineer peptide variants, evaluating their effectiveness and stability as therapeutic agents.

Protein Engineering: Delving into the domain of protein manipulation, Fmoc-β-(3-thienyl)-L-alanine plays a vital role in introducing thiophene motifs into proteins for in-depth structural and functional investigations. This avenue enables scientists to probe protein-ligand interactions and delve into protein folding mechanisms. Furthermore, the thiophene group provides a canvas for further chemical alterations or bioconjugation, expanding the possibilities in protein engineering.

Materials Science: In the captivating terrain of materials science, Fmoc-β-(3-thienyl)-L-alanine acts as a catalyst for the creation of trailblazing biomaterials imbued with unique electronic properties. Its integration into peptides or polypeptides can yield conductive or semiconductive polymers, opening new avenues in biosensors, electronic devices, and specialized coatings. This intersection of disciplines offers exciting prospects for cutting-edge applications.

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