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Application Area

Z-β-cyclohexyl-D-alanine dicyclohexylammonium salt

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

Category

CBZ-Amino Acids

Catalog number

BAT-005794

CAS number

214852-64-9

Molecular Formula

C7H23NO4·C12H23N

Molecular Weight

486.52

Z-β-cyclohexyl-D-alanine dicyclohexylammonium salt

IUPAC Name

N-cyclohexylcyclohexanamine;(2R)-3-cyclohexyl-2-(phenylmethoxycarbonylamino)propanoic acid

Synonyms

Z-D-Cha-OH DCHA; Z-3-cyclohexyl-D-alanine dicyclohexylammonium salt

Purity

≥ 98% (HPLC)

Melting Point

155-161 °C

Storage

Store at 2-8°C

InChI

InChI=1S/C17H23NO4.C12H23N/c19-16(20)15(11-13-7-3-1-4-8-13)18-17(21)22-12-14-9-5-2-6-10-14;1-3-7-11(8-4-1)13-12-9-5-2-6-10-12/h2,5-6,9-10,13,15H,1,3-4,7-8,11-12H2,(H,18,21)(H,19,20);11-13H,1-10H2/t15-;/m1./s1

InChI Key

IDRYYPLNVRWFOR-XFULWGLBSA-N

Canonical SMILES

C1CCC(CC1)CC(C(=O)O)NC(=O)OCC2=CC=CC=C2.C1CCC(CC1)NC2CCCCC2

Z-β-cyclohexyl-D-alanine dicyclohexylammonium salt, an extraordinary compound with a plethora of distinctive properties and diverse applications, stands as a prominent player in multiple domains. Here are the key applications presented with high perplexity and burstiness:

Peptide Synthesis: Positioned as a critical chiral building block in the intricate domain of peptide synthesis, Z-β-cyclohexyl-D-alanine dicyclohexylammonium salt lends its distinctive cyclohexyl group to the mix. This group's steric hindrance assumes a pivotal role in shaping specific peptide conformations solidifying its status as a coveted asset in the production of peptide-based drugs and bioactive peptides aimed at revolutionizing modern medical practices.

Chiral Catalysis: Embracing its versatile identity as a ligand in the realm of asymmetric synthesis, this compound engages in a graceful dance with metal catalysts to orchestrate the generation of enantiomerically pure compounds. Through this harmonious collaboration the compound amplifies the selectivity and efficiency of catalytic reactions-an indispensable aspect in pharmaceutical and agrochemical synthesis where chiral purity reigns supreme heralding a new era of chemical precision.

Pharmaceutical Research: Within the expansive realm of pharmaceutical exploration, Z-β-cyclohexyl-D-alanine dicyclohexylammonium salt emerges as a beacon of experimentation and ingenuity. Its exceptional chemical structure partakes in a symphony of interactions with diverse biological targets illuminating intricate drug-receptor dynamics. Armed with this profound understanding, researchers forge the path towards novel therapeutic agents distinguished by heightened specificity and diminished side effects marking a breakthrough in pharmaceutical discovery.

Materials Science: Venturing into the intricate realm of materials science, this compound assumes a pivotal role in the expansive tapestry of innovation. Serving as a transformative force in surface modification and material advancement, it ushers in materials imbued with unparalleled attributes. Whether integrated into polymers or coatings it introduces chirality and enhances mechanical or optical characteristics propelling advancements in electronics optics and biomaterials paving the way for a future shaped by cutting-edge materials.

1.The birth of flow-directed thermodilution catheters: how measurement of cardiac output became a routine procedure.

Berthelsen PG1. Acta Anaesthesiol Scand. 2015 Oct;59(9):1116-8. doi: 10.1111/aas.12513.

2.GABAergic Pharmacotherapy in the Treatment of Motor Disorders of the Central Nervous System.

Gazulla J1, Ruiz-Gazulla C, Tintore M. Curr Pharm Des. 2015;21(34):4989-95.

Gamma-aminobutyric acid (GABA) is the main inhibitory neurotransmitter in the central nervous system, and diseases that associate a deficiency in GABA might benefit from GABAergic drugs. Cerebellar Purkinje cells employ GABA as a neurotransmitter. Cortical cerebellar atrophy (CCA) shows Purkinje cell loss, and ataxia caused by it was alleviated by gabapentin and pregabalin. Thus, CCA is proposed as a model of selective deficiency in GABA in the cerebellum, which benefits clinically from administration of GABAergic drugs, in a manner similar in which levodopa improves motor manifestations in Parkinson's disease. Other ataxias also benefited clinically from GABAergic drugs, as adult-onset GM2 gangliosidosis, olivopontocerebellar atrophy, cerebellar ataxia with hypogonadism, spinocerebellar ataxias 1, 2 and 6, and adult-onset ataxia-telangiectasia. Complex neurochemical diseases, as multiple-system atrophy, had ataxia worsened by GABAergic drugs.

3.NO is involved in spermidine-induced drought tolerance in white clover via activation of antioxidant enzymes and genes.

Peng D1, Wang X, Li Z, Zhang Y, Peng Y, Li Y, He X, Zhang X, Ma X, Huang L, Yan Y. Protoplasma. 2015 Sep 4. [Epub ahead of print]

Nitric oxide (NO), a key signaling molecule, can be induced by polyamines (PAs), which play an important role in improving drought tolerance in plants. This study was to further investigate the role of NO in spermidine (Spd)-induced drought tolerance associated with antioxidant defense in leaves of white clover (Trifolium repens) under drought stress induced by -0.3 MPa polyethylene glycol (PEG-6000) solution. A hydroponic growth method was used for cultivating plants in a controlled growth chamber for 30-33 days until the second leaves were fully expanded. Two relative independent experiments were carried out in our study. One is that exogenous application of Spd or an NO donor (sodium nitroprusside (SNP)) significantly improved drought tolerance in whole plants, as demonstrated by better phenotypic appearance, increased relative water content (RWC), and decreased electrolyte leakage (EL) and malondialdehyde (MDA) content in leaves as compared to untreated plants.

4.Bovine lactoferrin regulates cell survival, apoptosis and inflammation in intestinal epithelial cells and preterm pig intestine.

Nguyen DN1, Jiang P2, Stensballe A3, Bendixen E4, Sangild PT2, Chatterton DE5. J Proteomics. 2016 Apr 29;139:95-102. doi: 10.1016/j.jprot.2016.03.020. Epub 2016 Mar 17.

Bovine lactoferrin (bLF) may modulate neonatal intestinal inflammation. Previous studies in intestinal epithelial cells (IECs) indicated that moderate bLF doses enhance proliferation whereas high doses trigger inflammation. To further elucidate cellular mechanisms, we profiled the porcine IEC proteome after stimulation with bLF at 0, 0.1, 1 and 10g/L by LC-MS-based proteomics. Key pathways were analyzed in the intestine of formula-fed preterm pigs with and without supplementation of 10g/L bLF. Levels of 123 IEC proteins were altered by bLF. Low bLF doses (0.1-1g/L) up-regulated 11 proteins associated with glycolysis, energy metabolism and protein synthesis, indicating support of cell survival. In contrast, a high bLF dose (10g/L) up-regulated three apoptosis-inducing proteins, down-regulated five anti-apoptotic and proliferation-inducing proteins and 15 proteins related to energy and amino acid metabolism, and altered three proteins enhancing the hypoxia inducible factor-1 (HIF-1) pathway.