Fmoc-β-(2-thienyl)-L-alanine
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Fmoc-β-(2-thienyl)-L-alanine

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Category
Fmoc-Amino Acids
Catalog number
BAT-007501
CAS number
130309-35-2
Molecular Formula
C22H19NO4S
Molecular Weight
393.46
Fmoc-β-(2-thienyl)-L-alanine
IUPAC Name
(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-thiophen-2-ylpropanoic acid
Synonyms
Fmoc-3-L-Ala(2-thienyl)-OH; Fmoc-3-(2-thienyl)-L-alanine
Related CAS
201532-42-5 (D-isomer)
Appearance
White to off-white powder
Purity
≥ 99% (HPLC, Chiral purity)
Density
1.343 g/cm3
Melting Point
218.5°C
Boiling Point
623.4°C at 760 mmHg
Storage
Store at 2-8 °C
InChI
InChI=1S/C22H19NO4S/c24-21(25)20(12-14-6-5-11-28-14)23-22(26)27-13-19-17-9-3-1-7-15(17)16-8-2-4-10-18(16)19/h1-11,19-20H,12-13H2,(H,23,26)(H,24,25)/t20-/m0/s1
InChI Key
PXBMQFMUHRNKTG-FQEVSTJZSA-N
Canonical SMILES
C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)NC(CC4=CC=CS4)C(=O)O

Fmoc-β-(2-thienyl)-L-alanine, an amino acid derivative crucial in peptide synthesis and medicinal chemistry, boasts diverse applications that showcase high perplexity and burstiness.

Peptide Synthesis: Embedded in solid-phase peptide synthesis (SPPS), Fmoc-β-(2-thienyl)-L-alanine acts as a fundamental building block. This enables the integration of β-amino acids into peptide sequences, elevating the stability and bioactivity of the peptides. Researchers harness this derivative to craft innovative peptides with promising therapeutic potentials, ushering in a new era of peptide design.

Drug Development: A cornerstone in drug development, this amino acid derivative plays a pivotal role in shaping peptidomimetics—compounds that mimic peptide structures yet exhibit enhanced stability and resistance to enzymatic breakdown. By infusing Fmoc-β-(2-thienyl)-L-alanine into peptidomimetics, researchers can engineer drug candidates with superior pharmacokinetic and pharmacodynamic profiles. Such compounds hold promise in combatting a myriad of diseases like cancer and metabolic disorders, offering renewed hope for patients.

Structural Biology: Within the realm of structural biology, Fmoc-β-(2-thienyl)-L-alanine emerges as a potent tool for introducing specific functional groups into peptides, thereby probing protein-ligand interactions. This facilitates a deeper understanding of binding affinities and conformational dynamics of target proteins. By leveraging this derivative, scientists can craft inhibitors or activators rooted in their binding studies, unlocking pathways towards novel therapeutic interventions.

Chemical Biology: In the realm of chemical biology, Fmoc-β-(2-thienyl)-L-alanine plays a pivotal role in unraveling enzyme-substrate interactions and protein modifications. By incorporating it into peptides serving as substrates or probes for enzyme activity assays, researchers shed light on enzyme mechanisms and unearth potential inhibitors. This application propels our comprehension of biological processes at the molecular level, providing insights that pave the way for groundbreaking discoveries.

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