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Application Area

D-Cyclohexylalaninol

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

Category

Amino Alcohol

Catalog number

BAT-002636

CAS number

205445-49-4

Molecular Formula

C9H19NO

Molecular Weight

157.26

IUPAC Name

(2R)-2-amino-3-cyclohexylpropan-1-ol

Synonyms

H-D-Cha-ol; H-D-Phe(hexahydro)-ol; D-Cyclohexylalaninol; (R)-2-Amino-3-cyclohexyl-1-propanol

Purity

97%

Density

0.970 g/cm3

Boiling Point

289.0 °C

InChI

InChI=1S/C9H19NO/c10-9(7-11)6-8-4-2-1-3-5-8/h8-9,11H,1-7,10H2/t9-/m1/s1

InChI Key

QWDRYURVUDZKSG-SECBINFHSA-N

Canonical SMILES

C1CCC(CC1)CC(CO)N

D-Cyclohexylalaninol, an amino alcohol compound with diverse applications in the bioscience industry, is instrumental in various fields. Here are the key applications presented with high perplexity and burstiness:

Chiral Synthesis: Renowned for its role in chiral synthesis, D-Cyclohexylalaninol acts as a pivotal chiral building block in organic synthesis. Its distinctive stereochemistry and complex structure render it invaluable for crafting enantiomerically pure pharmaceutical compounds. This precise attribute guarantees the production of drugs with heightened efficacy and minimized side effects revolutionizing the pharmaceutical landscape.

Catalyst Development: Unveiling new realms of possibility in chemical research, D-Cyclohexylalaninol emerges as a catalyst for developing chiral catalysts tailored for enantioselective reactions. These catalysts play a pivotal role in asymmetric synthesis facilitating the production of specific enantiomers vital for target molecules. Such applications hold significant sway in refining fine chemicals and advancing pharmaceutical formulations with unparalleled precision.

Biochemical Research: Serving as a cornerstone in biochemical studies, D-Cyclohexylalaninol emerges as a potent probe in unraveling enzyme mechanisms and protein-ligand interactions. Researchers harness its properties to delve into the intricate processes through which enzymes recognize and process chiral substrates shedding light on crucial aspects of enzymatic functions. This knowledge fuels the design of enzyme modulators and bioactive molecules propelling breakthroughs in drug development and molecular research.

Pharmaceutical Formulation: Spearheading advancements in pharmaceutical formulation, D-Cyclohexylalaninol integrates seamlessly into drug development processes to enhance the solubility and stability of active pharmaceutical ingredients (APIs). Its unique characteristics pave the way for heightened bioavailability of drugs amplifying their efficacy in clinical settings. Particularly beneficial for oral dosage forms and sustained-release formulations D-Cyclohexylalaninol plays a pivotal role in revolutionizing drug delivery systems and optimizing therapeutic outcomes.

1.Experimental evaluation of CH-π interactions in a protein core.

Pace CJ1, Kim D, Gao J. Chemistry. 2012 May 7;18(19):5832-6. doi: 10.1002/chem.201200334. Epub 2012 Mar 30.

CH-π stacks up! Using the protein α(2) D as a model system, we estimate that a CH-π contact between cyclohexylalanine (Cha) and phenylalanine (F) contributes approximately -0.7 kcal mol(-1) to the protein stability. The stacking F-Cha pairs are sequestered in the core of the protein, where water interference does not exist (see figure). Therefore, the observed energetic gain should represent the inherent magnitude and upper limit of the CH-π interactions.

2.Assessment of structurally diverse philanthotoxin analogues for inhibitory activity on ionotropic glutamate receptor subtypes: discovery of nanomolar, nonselective, and use-dependent antagonists.

Frølund S1, Bella A, Kristensen AS, Ziegler HL, Witt M, Olsen CA, Strømgaard K, Franzyk H, Jaroszewski JW. J Med Chem. 2010 Oct 28;53(20):7441-51. doi: 10.1021/jm100886h.

An array of analogues of the wasp toxin philanthotoxin-433, in which the asymmetric polyamine moiety was exchanged for spermine and the headgroup replaced with a variety of structurally diverse moieties, was prepared using parallel solid-phase synthesis approaches. In three analogues, the spermine moiety was extended with an amino acid tail, six compounds contained an N-acylated cyclohexylalanine, and four analogues were based on a novel diamino acid design with systematically changed spacer length between N-cyclohexylcarbonyl and N-phenylacetyl substituents. The analogues were studied using two-electrode voltage-clamp electrophysiology employing Xenopus laevis oocytes expressing GluA1(i) AMPA or GluN1/2A NMDA receptors. Several of the analogues showed significantly increased inhibition of the GluN1/2A NMDA receptor. Thus, an analogue containing N-(1-naphtyl)acetyl group showed an IC(50) value of 47 nM. For the diamino acid-based analogues, the optimal spacer length between two N-acyl groups was determined, resulting in an analogue with an IC(50) value of 106 nM.

3.Bifunctional μ/δ opioid peptides: variation of the type and length of the linker connecting the two components.

Ding J1, Lemieux C, Chung NN, Schiller PW. Chem Biol Drug Des. 2012 Feb;79(2):186-93. doi: 10.1111/j.1747-0285.2011.01268.x. Epub 2012 Jan 4.

On the basis of evidence that opioid compounds with a mixed μ agonist/δ antagonist profile may produce an antinociceptive effect with low propensity to induce side effects, bifunctional opioid peptides containing the μ agonist H-Dmt-d-Arg-Phe-Lys-NH(2) ([Dmt(1) ]DALDA; Dmt = 2',6'-dimethyltyrosine) connected tail-to-tail via various α,ω-diaminoalkyl- or diaminocyclohexane linkers to the δ antagonists H-Tyr-TicΨ[CH(2) -NH]Cha-Phe-OH (TICP[Ψ]; Cha = cyclohexylalanine, Tic = 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid), H-Dmt-Tic-OH or H-Bcp-Tic-OH (Bcp = 4'-[N-((4'-phenyl)phenethyl)carboxamido]phenylalanine) were synthesized and pharmacologically characterized in vitro. Bifunctional [Dmt(1) ]DALDA→NH-(CH(2) )(n) -NH←TICP[Ψ] compounds (n = -12) showed decreasing μ and δ receptor binding affinities with increasing linker length. As expected, several of the bifunctional peptides were μ agonist/δ antagonists with low nanomolar μ and δ receptor binding affinities.