β-Cyclohexyl-D-alanine hydrochloride
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β-Cyclohexyl-D-alanine hydrochloride

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Category
D-Amino Acids
Catalog number
BAT-005817
CAS number
151899-07-9
Molecular Formula
C9H17NO2·HCl
Molecular Weight
207.70
β-Cyclohexyl-D-alanine hydrochloride
IUPAC Name
(2R)-2-amino-3-cyclohexylpropanoic acid;hydrochloride
Synonyms
D-Cha-OH HCl; 3-Cyclohexyl-D-alanine hydrochloride
Appearance
White to off-white crystalline powder
Purity
≥ 97% (Assay by titration)
Boiling Point
307.1°C at 760 mmHg
Storage
Store at 2-8°C
InChI
InChI=1S/C9H17NO2.ClH/c10-8(9(11)12)6-7-4-2-1-3-5-7;/h7-8H,1-6,10H2,(H,11,12);1H/t8-;/m1./s1
InChI Key
QNGGSVANUAULGK-DDWIOCJRSA-N
Canonical SMILES
C1CCC(CC1)CC(C(=O)O)N.Cl

β-Cyclohexyl-D-alanine hydrochloride, a specialized amino acid derivative, finds diverse applications in bioscience and biotechnology. Here are the key applications presented with high perplexity and burstiness:

Peptide Synthesis: A staple in peptide synthesis, β-Cyclohexyl-D-alanine hydrochloride plays a pivotal role in crafting custom peptides for both research and therapeutic endeavors. Its integration into peptide sequences bestows distinct structural characteristics and bolsters peptide stability, rendering it indispensable in the creation of innovative peptides endowed with precise biological activities.

Pharmaceutical Development: Within the realm of drug discovery, β-Cyclohexyl-D-alanine hydrochloride emerges as a fundamental constituent for synthesizing peptidomimetics and small-molecule therapeutics. Leveraging its unique chemical attributes, researchers exploit this compound as a cornerstone for enhancing the pharmacokinetic and pharmacodynamic profiles of drug candidates, aiding in the design of potent and selective pharmaceutical agents.

Protein Engineering: Delving into the intricate domain of protein engineering, β-Cyclohexyl-D-alanine hydrochloride serves as a catalyst for unraveling the intricate structure-function correlations within proteins. Through the incorporation of this non-standard amino acid into proteins, scientists explore its impact on protein folding, stability, and enzymatic activity, crucial for deciphering protein functionalities and engineering novel proteins with augmented properties.

Biocatalysis Research: At the forefront of biocatalysis, β-Cyclohexyl-D-alanine hydrochloride is harnessed to probe enzyme specificity and catalytic mechanisms. Enzymes modified with this amino acid derivative demonstrate modified substrate specificity and enhanced catalytic efficiency, facilitating the design of tailored biocatalysts for diverse industrial applications, including the synthesis of pharmaceuticals and fine chemicals, ushering in a new era of enzymatic innovation.

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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