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Application Area

β-(2-Thienyl)-L-alanine

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

Category

L-Amino Acids

Catalog number

BAT-005809

CAS number

22951-96-8

Molecular Formula

C7H9NO2S

Molecular Weight

171.20

IUPAC Name

(2S)-2-amino-3-thiophen-2-ylpropanoic acid

Synonyms

3-L-Ala(2-thienyl)-OH; (S)-α-Amino-2-thiophenepropionic acid

Appearance

Off-white crystals

Purity

≥ 99.5% (HPLC, Chiral purity)

Melting Point

255±4 °C (dec.)

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-/m0/s1

InChI Key

WTOFYLAWDLQMBZ-LURJTMIESA-N

Canonical SMILES

C1=CSC(=C1)CC(C(=O)O)N

β-(2-Thienyl)-L-alanine (BTA) is an amino acid analog that has garnered considerable interest due to its unique chemical structure and properties. One of its primary applications is in the field of medicinal chemistry. BTA has been investigated as a potential pharmacophore for designing new drugs because its thienyl group can engage in π-π interactions and hydrogen bonding, crucial for the stability and activity of many drug molecules. Moreover, its structural resemblance to naturally occurring amino acids allows it to be incorporated into peptides and proteins, potentially leading to the development of novel therapeutic agents with improved efficacy and selectivity.

Another significant application of β-(2-Thienyl)-L-alanine is in biochemical research, particularly in the study of enzyme mechanisms and protein structures. BTA can serve as a site-specific probe to investigate enzyme-substrate interactions. By substituting BTA for its natural amino acid counterparts in enzyme active sites, researchers can analyze changes in activity and binding, providing insights into the roles of specific residues in catalysis and substrate recognition. This can ultimately aid in the design of enzyme inhibitors or the engineering of enzymes with enhanced properties for industrial or pharmaceutical applications.

The third critical area where β-(2-Thienyl)-L-alanine is used is in the field of materials science. BTA can be utilized to synthesize novel polymeric materials with unique electronic and mechanical properties. The presence of the thienyl group allows for π-conjugation along the polymer chain, which can enhance electrical conductivity and make these materials suitable for applications in organic electronics, such as organic light-emitting diodes (OLEDs), solar cells, and field-effect transistors (OFETs). Additionally, incorporating BTA into polymers can improve their mechanical strength and thermal stability, expanding their potential applications in various high-performance materials.

Lastly, β-(2-Thienyl)-L-alanine has applications in the field of agricultural sciences. BTA derivatives have been investigated for their potential as plant growth regulators and biopesticides. The unique chemical properties of BTA allow it to interact with plant biochemical pathways, potentially promoting growth or enhancing resistance to pests and diseases. Furthermore, BTA-based compounds can be used as a tool in agricultural research to study the effects of various amino acid analogs on plant physiology and development. This research could lead to the creation of more effective and sustainable agricultural practices, contributing to increased crop yields and reduced reliance on traditional chemical pesticides.

1. A CD and an NMR study of multiple bradykinin conformations in aqueous trifluoroethanol solutions

J R Cann, X Liu, J M Stewart, L Gera, G Kotovych Biopolymers. 1994 Jul;34(7):869-78. doi: 10.1002/bip.360340706.

CD and nmr studies have been carried out on aqueous trifluoroethanol (TFE) solutions of bradykinin (BK) and a bradykinin antagonist. The CD results exhibit a striking effect of TFE on the spectra of BK, with sequence Arg-Pro-Pro-Gly-Phe-Ser-Pro-Phe-Arg, and the BK antagonist, with sequence D-Arg-Arg-Pro-Hyp-Gly-Thi-D-Ser-D-Cpg-Cpg-Arg [where Hyp is 4-hydroxy-L-proline; Thi refers to beta-(2-thienyl)-L-alanine and Cpg refers to alpha-cyclopentylglycine). The effect of increasing concentration of TFE in water on the difference ellipticity at 222 nm was examined and showed that BK may be a mixture of at least two different conformers, one of which largely forms when the TFE concentration is increased beyond 80%. The linear extrapolation of 100% of the difference ellipticity of BK at low TFE concentrations yields a value in agreement with that shown by the BK antagonist, indicating that the conformation of BK at the lower TFE concentrations is similar to that of the BK antagonist. The conformational analysis was carried out using both one-dimensional and two-dimensional 1H-nmr techniques. The total correlation spectroscopy (TOCSY) spectrum of BK in a 60/40% (v/v) TFE/H2O solution at 10 degrees C and a nuclear Overhauser effect spectroscopy (NOESY) spectrum that shows only sequential H alpha (i)-NH(i + 1) or the H alpha (i)-H delta delta' (i + 1) NOEs indicate that the majority of the molecules adopt an all-trans extended conformation. The TOCSY for BK in the 95/5% (v/v) TFE/H2O solution shows that there are two major conformations in the solution with about equal population. The NOESY experiment shows two new important cross peaks for one conformation, namely Pro2 (alpha)-Pro3 (alpha) and the Pro2 (alpha)-Gly4(NH), indicating a cis Pro2-Pro3 bond and a type VI beta-turn between residues Arg1 and Gly4 involving cis proline at position 3, respectively. The low temperature coefficient of Gly4 for this conformation suggests the presence of an intramolecular hydrogen bond, therefore a type VIa beta-turn is present. The other conformation is all trans and extended. The BK antagonist shows difference CD spectra in TFE solutions referred to H2O that are superficially indicative of a beta-bend.(ABSTRACT TRUNCATED AT 400 WORDS)

2. Synthesis and some pharmacological properties (4-beta-(2-thienyl)-L-alanine)oxytocin

C W Smith, G Skala, R Walter J Med Chem. 1978 Jan;21(1):115-7. doi: 10.1021/jm00199a022.

The synthesis and some biological activities of [4-beta-(2-thienyl)-L-alanine]oxytocin are reported. This analogue has been studied in an ongoing exploration of the biological effects of introducing amino acid residues with bulky hydrophobic side chains into the second corner position of the beta turn present in the conformation of the 20-membered ring portion of oxytocin. The analogue was synthesized in stepwise manner by solution techniques utilizing ethylcarbamoyl protection for cysteine side chains. The presence of thienylalanine in position 4 evokes a drastic reduction in both affinity and intrinsic activity; the reduction in intrinsic activity was greater than that found for [Leu4]oxytocin or [Phe4]oxytocin. The analogue possesses 0.51 +/- 0.03 unit/mg of rat uterotonic potency and less than 0.05 unit/mg of rat pressor and rat antidiuretic potency and behaves as a competitive inhibitor of the response to oxytocin in the avian vasodepressor assay with a pA2 value of 7.44 +/- 0.19.

3. Synthesis and some pharmacological properties of (3-beta-(2-thienyl)-L-alanine)-8-lysine-vasopressin

C W Smith, M F Ferger, W Y Chan J Med Chem. 1975 Aug;18(8):822-5. doi: 10.1021/jm00242a012.

[3-beta-(2-Thienyl)-L-alanine]-8-lysine-vasopressin was synthesized by solution techniques. The partially protected heptapeptide Boc-Cys(Ec)-Tyr-Thi-Gln-Asn-Cys(Ec)-Pro (1) was synthesized in a stepwise manner using the active ester method or the dicyclohexylcarbodiimide (DCC) coupling technique mediated by 1-hydroxybenzotriazole (HBt). The protected nonapeptide amide Boc-Cys(Ec)-Tyr-Thi-Gin-Asn-Cys(Ec)-Pro-Lys(Coc)-Gly-NH2 (2) was prepared by coupling 1 with Lys(Coc)-Gly-NH2 using DCC-HBt. From 2, [3-thienylalanine]-8-lysine-vasopressin was obtained by removing the Boc-protecting groups with trifluoroacetic acid and ethylcarbamoyl (Ec) protecting groups in refluxing liquid NH3 followed by oxidative cyclization in H2O-MeOH using ICH2CH2I. Purification was effected by partition chromatography followed by gel filtration. The highly purified product possesses activities in the oxytocic, avian vasodepressor, rat pressor, and antidiuretic assays of 19.0 +/- 0.5, 87 +/- 4, 243 +/- 5, and 332 +/- 32 units/mg, respectively. Thus [3-thienylalanine]-8-lysine-vasopressin has higher oxytocic, avian vasodepressor, and antidiuretic potencies than does 8-lysine-vasopressin, whereas its pressor potency is about the same as or slightly lower than that of 8-lysine-vasopressin.