γ-Styryl-L-β-homoalanine hydrochloride
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γ-Styryl-L-β-homoalanine hydrochloride

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Category
β−Amino Acids
Catalog number
BAT-002568
CAS number
332064-69-4
Molecular Formula
C12H16ClNO2
Molecular Weight
241.71
IUPAC Name
(E,3S)-3-amino-6-phenylhex-5-enoic acid;hydrochloride
Synonyms
H-Ala(Styryl)-OH HCl; H-Phe(#5,6=CH)-OH HCl; (S)-3-Amino-6-phenyl-5-hexenoic acid hydrochloride
InChI
InChI=1S/C12H15NO2.ClH/c13-11(9-12(14)15)8-4-7-10-5-2-1-3-6-10;/h1-7,11H,8-9,13H2,(H,14,15);1H/b7-4+;/t11-;/m0./s1
InChI Key
OREIHEVSPFNFKW-OSVHXEEUSA-N
Canonical SMILES
C1=CC=C(C=C1)C=CCC(CC(=O)O)N.Cl

γ-Styryl-L-β-homoalanine hydrochloride, a synthetic amino acid derivative with exceptional properties, finds diverse applications in bioscience research.

Protein Conformational Studies: Delving into protein structure and dynamics, researchers utilize γ-Styryl-L-β-homoalanine hydrochloride for its distinct styryl group that enables fluorescence tagging. This unique feature allows scientists to monitor protein folding and interactions, offering deeper insights into protein conformational changes and functionality.

Drug Design and Development: Playing a pivotal role in drug innovation, this compound serves as a fundamental component for constructing synthetic peptides and proteins. Integration of γ-Styryl-L-β-homoalanine hydrochloride into peptide backbones enhances stability and bioactivity of therapeutic agents, fostering the creation of more potent and targeted treatments through structural modifications.

Enzyme Mechanism Studies: Scientists employ γ-Styryl-L-β-homoalanine hydrochloride to investigate enzyme active sites and unravel catalytic mechanisms. Its inclusion in substrate analogs provides valuable insights into enzyme specificity and mechanisms of action, laying the groundwork for designing enzyme modulators, such as inhibitors or activators.

Biomolecular Interactions: In the realm of biomolecular interactions, this compound serves as a vital tool for exploring binding events between biomolecules, like protein-protein or protein-ligand interactions. Leveraging the fluorescent properties of the styryl group, researchers use it as a dynamic probe for real-time studies on these interactions, offering critical insights into cellular processes and guiding the development of therapeutic interventions.

1. Metal-free and regiospecific synthesis of 3-arylindoles
Chuangchuang Xu, Wenlai Xie, Jiaxi Xu Org Biomol Chem. 2020 Apr 8;18(14):2661-2671. doi: 10.1039/d0ob00317d.
A convenient, metal-free, and organic acid-base promoted synthetic method to prepare 3-arylindoles from 3-aryloxirane-2-carbonitriles and arylhydrazine hydrochlorides has been developed. In the reaction, the organic acid catalyzes a tandem nucleophilic ring-opening reaction of aryloxiranecarbonitriles and arylhydrazine hydrochlorides and Fischer indolization. The organic base triethylamine plays a crucial role in the final elimination step in the Fischer indole synthesis, affording 3-arylindoles regiospecifically. The reaction features advantages of microwave acceleration, non-metal participation, short reaction time, organic acid-base co-catalysis, and broad substrate scope.
2. 1-Haloacylpiperazines
S Groszkowski, J Sienkiewicz, L Korzycka Pol J Pharmacol Pharm. 1975 Apr-Jun;27(2):183-6.
By direct acylation of piperazine with halogenocarboxylic acid chlorides in acid medium, the hydrochlorides of 1-haloacylpiperazines were obtained.
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