3-Benzothienyl-D-alanine
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3-Benzothienyl-D-alanine

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3-Benzothienyl-D-alanine is a useful intermediate used in the preparation of enantiopure L-benzofuranyl-and L-benzothienyl alanines.

Category
D-Amino Acids
Catalog number
BAT-007824
CAS number
111139-55-0
Molecular Formula
C11H11NO2S
Molecular Weight
221.28
3-Benzothienyl-D-alanine
IUPAC Name
(2R)-2-amino-3-(1-benzothiophen-3-yl)propanoic acid
Synonyms
3-D-Ala(3-benzothienyl)-OH; (R)-2-Amino-3(benzo[β]thiophen-3-yl)propionic acid; 3-(3-Benzothienyl)-D-alanine; D-3-BENZOTHIENYLALANINE; D-3-(3-Benzothienyl)alanine; (R)-2-Amino-3(benzo[b]thiophen-3-yl)-propionic acid; (2R)-2-azanyl-3-(1-benzothiophen-3-yl)propanoic acid; 3-(Benzo[b]thiophen-3-yl)-L-alanine; d-3-benzothienyl-alanine; H-D-Ala(3-Bzt)-OH
Related CAS
72120-71-9 (L-isomer)
Appearance
Almost white powder
Purity
≥ 99% (Assay on anhydrous basis)
Density
1.374±0.06 g/cm3 (Predicted)
Melting Point
236-240 °C
Boiling Point
416.7 °C at 760 mmHg
Storage
Store at 2-8 °C
InChI
InChI=1S/C11H11NO2S/c12-9(11(13)14)5-7-6-15-10-4-2-1-3-8(7)10/h1-4,6,9H,5,12H2,(H,13,14)/t9-/m1/s1
InChI Key
GAUUPDQWKHTCAX-SECBINFHSA-N
Canonical SMILES
C1=CC=C2C(=C1)C(=CS2)CC(C(=O)O)N

3-Benzothienyl-D-alanine, a synthetic amino acid, finds diverse applications in bioscience and pharmaceutical domains. Here are the key applications articulated with high perplexity and burstiness:

Drug Development: Harnessing the potential of 3-Benzothienyl-D-alanine as a foundational component in synthesizing cutting-edge pharmaceutical compounds, researchers unlock the ability to craft molecules with precise therapeutic attributes. This compound's unique configuration facilitates the creation of novel drug candidates tailored for specific biological targets, elevating drug effectiveness and specificity to new heights.

Peptide Synthesis: Within the realm of peptide synthesis, the integration of 3-Benzothienyl-D-alanine empowers scientists to delve into the intricate relationships between structure and function. By introducing this synthetic amino acid into peptides, researchers imbue these molecules with distinct chemical properties and enhanced stability. This application is pivotal for sculpting peptides with heightened therapeutic efficacy and prolonged biological activity, pushing the boundaries of peptide-based therapeutics.

Enzyme Inhibition Studies: Serving as a cornerstone in enzyme inhibition investigations, 3-Benzothienyl-D-alanine emerges as a pivotal tool for probing the intricacies of enzyme function. Whether acting as a competitive inhibitor or mimicking a substrate, this compound aids in the precise mapping and characterization of enzyme active sites. Researchers leverage its capabilities to unravel the nuances of enzyme kinetics and mechanisms, paving the way for tailored enzyme-targeted therapies that hold the promise of groundbreaking advancements in healthcare.

Biomaterials Development: In the domain of materials science, the utilization of 3-Benzothienyl-D-alanine sparks innovation in the development of advanced biomaterials boasting unique attributes. Its integration into polymeric structures elevates the mechanical and chemical properties of these materials, opening new avenues for creating sophisticated biomaterials. This application is instrumental in crafting next-generation biomaterials for diverse applications ranging from medical devices to drug delivery systems and tissue engineering scaffolds, heralding a new era of biomaterial innovation.

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