β-Cyclohexyl-L-alaninamide hydrochloride
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β-Cyclohexyl-L-alaninamide hydrochloride

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Category
L-Amino Acids
Catalog number
BAT-002211
CAS number
119936-17-3
Molecular Formula
C9H19ClN2O
Molecular Weight
206.72
IUPAC Name
(2S)-2-amino-3-cyclohexylpropanamide;hydrochloride
Synonyms
H-Cha-NH2 HCl; H-Phe(hexahydro)-NH2 HCl; (S)-2-Amino-3-cyclohexylpropanamide hydrochloride; Hexahydro-L-phenylalaninamide hydrochloride
Purity
> 95%
Storage
Store at 2-8 °C
InChI
InChI=1S/C9H18N2O.ClH/c10-8(9(11)12)6-7-4-2-1-3-5-7;/h7-8H,1-6,10H2,(H2,11,12);1H/t8-;/m0./s1
InChI Key
HUKVBIJDEMXDKQ-QRPNPIFTSA-N
Canonical SMILES
C1CCC(CC1)CC(C(=O)N)N.Cl

β-Cyclohexyl-L-alaninamide hydrochloride, a versatile compound with myriad applications in bioscience and pharmaceutical research, plays a pivotal role in various fields. Here are the key applications presented with high perplexity and burstiness:

Peptide Synthesis: Serving as a foundational element in peptide synthesis, β-Cyclohexyl-L-alaninamide hydrochloride facilitates the creation of peptide chains by acting as a crucial building block. Its significance lies in the production of peptides with precise sequences essential for biochemical investigations and drug discovery. The compound's exceptional stability and reactivity make it an indispensable component in the intricate realm of peptide chemistry.

Pharmaceutical Research: Within the realm of pharmaceutical exploration, β-Cyclohexyl-L-alaninamide hydrochloride emerges as a key intermediate in the synthesis of diverse bioactive compounds. Leveraging its chemical attributes, researchers harness its potential to craft novel drug candidates with promising therapeutic effects. Integration of this compound into drug structures can optimize pharmacokinetic properties and enhance therapeutic efficacy, paving the way for groundbreaking pharmaceutical developments.

Enzyme Inhibition Studies: Delving into enzyme activities and inhibition mechanisms, β-Cyclohexyl-L-alaninamide hydrochloride finds application in probing the interactions between compounds and enzymes. By integrating this compound into enzyme assays, researchers dissect its impact on enzyme function, unraveling potential inhibitors that hold promise as drug candidates across various ailment spectra. These investigations are indispensable for identifying novel therapeutic avenues rooted in enzyme inhibition.

Chiral Catalyst Development: Positioned as a versatile chiral auxiliary and ligand, β-Cyclohexyl-L-alaninamide hydrochloride contributes significantly to the advancement of asymmetric catalysts. These catalysts play a vital role in driving enantioselective synthesis, enabling the precise production of chiral molecules with high selectivity. This application assumes particular significance in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals that necessitate specific stereochemical requirements, underscoring the compound's versatility and importance in catalysis research.

1. 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.
2. 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.
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