L-β-Homoalanine hydrochloride
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L-β-Homoalanine hydrochloride

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Category
β−Amino Acids
Catalog number
BAT-007589
CAS number
58610-41-6
Molecular Formula
C4H9NO2·HCl
Molecular Weight
139.58
L-β-Homoalanine hydrochloride
IUPAC Name
(3S)-3-aminobutanoic acid;hydrochloride
Synonyms
L-β-HomoAla-OH HCl; (S)-3-Aminobutyric acid hydrochloride; L-beta-Homoalanine hydrochloride; (s)-3-aminobutanoic acid hydrochloride; (S)-HOMO-BETA-ALANINE HCl; L-Beta-homoalanine HCl; (S)-3-amino-butanoic acid hydrochloride; Butanoic acid,3-amino-, hydrochloride (1:1), (3S)-; (3S)-3-aminobutanoic acid hydrochloride; L beta HomoAla OH HCl
Related CAS
3775-72-2 (free base)
Appearance
White powder
Purity
≥ 98% (NMR)
Boiling Point
223.6 °C at 760 mmHg
Storage
Store at 2-8 °C
InChI
InChI=1S/C4H9NO2.ClH/c1-3(5)2-4(6)7;/h3H,2,5H2,1H3,(H,6,7);1H/t3-;/m0./s1
InChI Key
UHYVVUABAWKTJJ-DFWYDOINSA-N
Canonical SMILES
CC(CC(=O)O)N.Cl

L-β-Homoalanine hydrochloride, a synthetic amino acid derivative, finds diverse applications in chemical and biological research. Here are the key applications presented with high perplexity and burstiness:

Peptide Synthesis: Serving as a foundational element in peptide synthesis, L-β-Homoalanine hydrochloride plays a pivotal role in constructing peptide sequences. Researchers utilize this compound to investigate structure-function correlations and advance the development of peptide-based pharmaceuticals. Through its incorporation into peptides, scientists can modify and optimize stability, bioactivity, and binding affinity, paving the way for innovative peptide design strategies.

Enzyme Inhibition Studies: Delving into the intricate mechanics of enzyme inhibition, L-β-Homoalanine hydrochloride is integrated into studies aimed at elucidating inhibition mechanisms. By introducing this compound into enzyme substrates, researchers can meticulously examine the specific interactions and inhibitory impacts on enzymes such as proteases. These investigations are fundamental in the quest to design and develop enzyme inhibitors as potential therapeutic interventions, offering insights into targeted enzyme modulation approaches.

Biological Function Studies: In the realm of biological function exploration, L-β-Homoalanine hydrochloride serves as a valuable tool for probing the roles of specific proteins and biological processes. Through the substitution of this amino acid analog in proteins, scientists can observe consequential changes in protein structure and functionality, shedding light on the contributions of different amino acid residues to protein activity and interplay. This method aids in unraveling the intricate web of protein functions and interactions, enhancing our understanding of the underlying biological mechanisms.

Metabolic Labeling: Crucial for metabolic investigations, L-β-Homoalanine hydrochloride functions as a labeled amino acid utilized to trace metabolic pathways within cellular systems. By incorporating this compound into cellular proteins, researchers can accurately monitor protein synthesis and degradation processes, providing crucial insights into protein dynamics and turnover across diverse biological contexts. This distinctive technique enables the in-depth exploration of metabolic processes, facilitating a nuanced understanding of protein metabolism dynamics and kinetics.

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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