b-Chloro-L-alanine hydrochloride
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b-Chloro-L-alanine hydrochloride

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Category
L-Amino Acids
Catalog number
BAT-007904
CAS number
51887-89-9
Molecular Formula
C3H6NO2Cl·HCl
Molecular Weight
160.00
b-Chloro-L-alanine hydrochloride
IUPAC Name
(2R)-2-amino-3-chloropropanoic acid;hydrochloride
Synonyms
b-Chloro-L-Ala-OH HCl; (R)-2-Amino-3-chloropropionic acid hydrochloride; 3-Chloro-L-alanine Hydrochloride; beta-Chloro-L-alanine hydrochloride; L-Alanine, 3-chloro-, hydrochloride; 3-Chloro-l-alanine HCl; H-Ala(3-Cl)-OH HCl
Related CAS
2731-73-9 (free base)
Appearance
White solid
Purity
≥ 95% (HPLC)
Density
1.401 g/cm3
Melting Point
205 °C (dec.)
Boiling Point
243.6 °C at 760 mmHg
Storage
Store at 2-8 °C
InChI
InChI=1S/C3H6ClNO2.ClH/c4-1-2(5)3(6)7;/h2H,1,5H2,(H,6,7);1H/t2-;/m0./s1
InChI Key
IENJPSDBNBGIEL-DKWTVANSSA-N
Canonical SMILES
C(C(C(=O)O)N)Cl.Cl

b-Chloro-L-alanine hydrochloride, an amino acid derivative with remarkable biological and chemical versatility, finds diverse applications in scientific research. Here are the key applications presented with high perplexity and burstiness:

Antibacterial Research: At the forefront of antibiotic investigations, b-Chloro-L-alanine hydrochloride plays a pivotal role in unraveling the mechanisms of antibiotics and bacterial resistance. Acting as a potent bacteriostatic agent, it disrupts bacterial cell wall synthesis, offering insights into bacterial growth dynamics. Researchers leverage this compound to probe how bacteria react to antibiotics, devising innovative strategies to combat the escalating threat of antibiotic resistance.

Enzyme Inhibition Studies: In the realm of enzyme inhibition research, b-Chloro-L-alanine hydrochloride emerges as a powerful tool. Serving as an irreversible inhibitor for specific enzymes, it provides scientists with a window into enzyme mechanisms and kinetics. This knowledge serves as a cornerstone for drug discovery, where enzyme inhibitors stand as prime targets for developing novel therapeutics, paving the way for groundbreaking pharmaceutical advancements.

Neurochemical Research: Delving into the intricate world of neurotransmitter pathways, b-Chloro-L-alanine hydrochloride takes center stage in probing the synthesis and metabolism of amino acids. With the ability to modulate the production of both excitatory and inhibitory neurotransmitters, this compound aids in deciphering neurological processes. Such insights enable the identification of potential targets for combatting neurological disorders, offering new avenues for therapeutic interventions in the realm of neurochemical research.

Biochemical Pathway Mapping: Offering a gateway to unraveling biochemical pathways and metabolic fluxes, b-Chloro-L-alanine hydrochloride facilitates detailed studies on metabolic processes. By integrating this compound into metabolic investigations, researchers can meticulously track and quantify various metabolic intermediates and end-products. This approach proves invaluable for metabolic engineering and systems biology, providing crucial insights into pathway optimization and metabolic control, driving forward the frontiers of biochemical research.

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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