Fmoc-3-benzothienyl-L-alanine
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Fmoc-3-benzothienyl-L-alanine

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Category
Fmoc-Amino Acids
Catalog number
BAT-007347
CAS number
177966-60-8
Molecular Formula
C26H21NO4S
Molecular Weight
443.51
Fmoc-3-benzothienyl-L-alanine
IUPAC Name
(2S)-3-(1-benzothiophen-3-yl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acid
Synonyms
Fmoc-3-L-Ala(3-benzothienyl)-OH
Related CAS
177966-61-9 (D-isomer)
Appearance
White to off-white solid
Purity
≥99.5% (Chiral HPLC)
Density
1.356 g/cm3
Boiling Point
690.8°C at 760 mmHg
Storage
Store at 2-8 °C
InChI
InChI=1S/C26H21NO4S/c28-25(29)23(13-16-15-32-24-12-6-5-7-17(16)24)27-26(30)31-14-22-20-10-3-1-8-18(20)19-9-2-4-11-21(19)22/h1-12,15,22-23H,13-14H2,(H,27,30)(H,28,29)/t23-/m0/s1
InChI Key
BQIZNDWONIMCGM-QHCPKHFHSA-N
Canonical SMILES
C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)NC(CC4=CSC5=CC=CC=C54)C(=O)O

Fmoc-3-benzothienyl-L-alanine, a modified amino acid widely utilized in peptide synthesis and biochemical research, offers a diverse range of applications. Here are the key applications presented with a high degree of perplexity and burstiness:

Peptide Synthesis: Utilizing Fmoc-3-benzothienyl-L-alanine in solid-phase peptide synthesis introduces a level of complexity to peptide chains, resulting in peptides with distinctive properties. Its benzothienyl side chain can induce hydrophobic interactions, leading to alterations in peptide conformation and stability. This capability enhances the design of peptides tailored for pharmaceutical and biochemical purposes, showcasing the intricate interplay between molecular components.

Protein-Protein Interaction Studies: The unique structural features of Fmoc-3-benzothienyl-L-alanine lend themselves to in-depth investigations of protein-protein interactions. By strategically integrating this amino acid into proteins or peptides at specific locations, researchers can elucidate how modifications impact binding affinities and the formation of complexes. This methodology is particularly valuable in the realms of drug discovery and structural biology, revealing the intricate dynamics of molecular interactions.

Bioconjugation: In the realm of bioconjugation, Fmoc-3-benzothienyl-L-alanine plays a crucial role in the synthesis of bioconjugates—hybrid molecules combining biological and synthetic elements. These bioconjugates serve as versatile tools, such as probes, therapeutic agents, or diagnostic aids, in diverse biomedical applications. The benzothienyl moiety's ability to interact with various functional groups facilitates the formation of stable conjugates, enhancing the adaptability and utility of these bioconjugates in complex biological systems.

Material Science: Within material science, Fmoc-3-benzothienyl-L-alanine finds application in the creation of innovative polymeric materials. Incorporating this modified amino acid into polymer chains enables the development of materials with unique electrical, optical, or mechanical properties. These novel materials hold promise for diverse applications in electronics, sensors, and biomaterials, showcasing the intersection of biological components with cutting-edge material engineering and paving the way for multifaceted advancements in material science.

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