β-(2-Thienyl)-D-alanine
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β-(2-Thienyl)-D-alanine

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β-(2-Thienyl)-D-alanine is an alanine derivative that is D-alanine in which one of the methyl hydrogens is replaced by a 2-thienyl group. It is a D-alpha-amino acid and a member of thiophenes. It derives from a D-alanine.

Category
D-Amino Acids
Catalog number
BAT-007772
CAS number
62561-76-6
Molecular Formula
C7H9NO2S
Molecular Weight
171.22
β-(2-Thienyl)-D-alanine
IUPAC Name
(2R)-2-amino-3-thiophen-2-ylpropanoic acid
Synonyms
3-D-Ala(2-thienyl)-OH; (R)-α-Amino-2-thiophenepropionic acid; 3-(2-Thienyl)-D-alanine; D-2-THIENYLALANINE; (R)-2-amino-3-(thiophen-2-yl)propanoic acid; beta-(2-Thienyl)-D-alanine; (2R)-2-amino-3-thiophen-2-ylpropanoic acid; H-D-Thi-OH; UNII-PJ4EM0CL5E; beta-2-thienyl-D-alanine
Appearance
White to off-white crystals
Purity
≥ 99% (HPLC)
Density
1.349 g/cm3
Melting Point
254-258 °C
Boiling Point
315.9 °C at 760 mmHg
Storage
Store at RT
InChI
InChI=1S/C7H9NO2S/c8-6(7(9)10)4-5-2-1-3-11-5/h1-3,6H,4,8H2,(H,9,10)/t6-/m1/s1
InChI Key
WTOFYLAWDLQMBZ-ZCFIWIBFSA-N
Canonical SMILES
C1=CSC(=C1)CC(C(=O)O)N

β-(2-Thienyl)-D-alanine, a derivative of the amino acid alanine, exhibits significant potential in various scientific and industrial fields. Here are some key applications of β-(2-Thienyl)-D-alanine:

Pharmaceutical Development: β-(2-Thienyl)-D-alanine can be used as a precursor or building block in the synthesis of pharmacologically active compounds. Its unique structural characteristics make it a valuable component in drug design, potentially leading to the development of novel therapeutic agents. Researchers study its activity to create new drugs with improved efficacy and reduced side effects.

Biocatalysis: This compound can be employed as a substrate or inhibitor in enzyme-catalyzed reactions, aiding in the study of enzyme mechanisms and kinetics. By utilizing β-(2-Thienyl)-D-alanine as a probe, researchers can gain insights into enzyme specificity and catalytic efficiency. This information is crucial for designing better biocatalysts and optimizing industrial bioprocesses.

Chemical Synthesis: β-(2-Thienyl)-D-alanine serves as an important intermediate in organic synthesis, enabling the construction of complex molecules. Its incorporation into synthetic routes can lead to the efficient production of diverse chemical entities, including natural products and polymers. The versatility of this compound supports advancements in materials science and synthetic chemistry.

Biological Research: This compound is beneficial in investigating the biological functions of amino acid analogs. By incorporating β-(2-Thienyl)-D-alanine into proteins, researchers can study conformational changes, protein folding, and interactions. Such studies are pivotal for understanding protein structure-function relationships and developing protein-based therapeutics.

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