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Boc-β-cyclopropyl-D-alanine DCHA

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

Category

BOC-Amino Acids

Catalog number

BAT-007189

CAS number

89483-09-0

Molecular Formula

C11H19NO4·C12H23N

Molecular Weight

410.60

IUPAC Name

N-cyclohexylcyclohexanamine;(2R)-3-cyclopropyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid

Synonyms

Boc-D-Ala(β-cyclopropyl)-OH dicyclohexylammonium salt; Boc-β-cyclopropyl-D-Ala-OH DCHA

Related CAS

89483-06-7 (L-isomer)

Appearance

White powder

Purity

≥ 99% (HPLC, Chiral purity)

Melting Point

155-161 °C

Boiling Point

377.2°C at 760 mmHg

Storage

Store at 2-8 °C

InChI

InChI=1S/C12H23N.C11H19NO4/c1-3-7-11(8-4-1)13-12-9-5-2-6-10-12;1-11(2,3)16-10(15)12-8(9(13)14)6-7-4-5-7/h11-13H,1-10H2;7-8H,4-6H2,1-3H3,(H,12,15)(H,13,14)/t;8-/m.1/s1

InChI Key

MQINYDUVLDJIAC-NIFFTEIASA-N

Canonical SMILES

CC(C)(C)OC(=O)NC(CC1CC1)C(=O)O.C1CCC(CC1)NC2CCCCC2

Boc-β-cyclopropyl-D-alanine DCHA, a specialized chemical intermediate, finds widespread use in bioscience and pharmaceuticals. Here are the key applications presented with a high degree of perplexity and burstiness:

Peptide Synthesis: Serving as a crucial building block in peptide synthesis, Boc-β-cyclopropyl-D-alanine DCHA is renowned for its ability to introduce unique conformational constraints due to its cyclopropyl group. This feature enhances the stability and bioactive properties of the resulting peptides, making it a valuable asset in the creation of peptide-based drugs and therapeutic agents. Its utilization in peptide synthesis underscores its significance in the realm of pharmaceutical development.

Drug Design and Development: Within the sphere of medicinal chemistry, Boc-β-cyclopropyl-D-alanine DCHA emerges as a pivotal intermediate for crafting novel compounds with potential therapeutic benefits. Its incorporation into drug candidates can significantly impact the biological activity selectivity and metabolic stability of the molecules. Researchers leverage this compound to explore uncharted pharmacophores and fine-tune lead compounds for enhanced drug discovery, underscoring its role in advancing pharmaceutical innovation.

Protease Inhibitor Research: Widely employed in synthesizing protease inhibitors crucial for combatting diseases like HIV/AIDS cancer and inflammatory disorders, Boc-β-cyclopropyl-D-alanine DCHA plays a vital role in drug development. By integrating this compound into inhibitor scaffolds, scientists can probe its effects on enzyme binding and inhibition paving the way for the creation of more potent and selective protease inhibitors. This application highlights the compound's importance in the fight against debilitating illnesses.

Chemical Biology: In the realm of chemical biology, Boc-β-cyclopropyl-D-alanine DCHA serves as a powerful tool for studying protein structures and functions through intricate chemical modifications. Its inclusion enables researchers to delve into protein-protein interactions and dynamics offering profound insights into complex biological processes. Through this application, scientists gain a deeper understanding of biochemical pathways and unearth novel molecular targets shaping the landscape of biological research.

1. A Novel Lithocholic Acid Derivative Upregulates Detoxification-Related Genes in Human Induced Pluripotent Stem Cell-Derived Intestinal Organoids

Shigeru Yamada, Hiroyuki Masuno, Hiroyuki Kagechika, Aya Tanatani, Yasunari Kanda Biol Pharm Bull. 2022;45(11):1720-1724. doi: 10.1248/bpb.b22-00492.

Vitamin D is a fat-soluble micronutrient that plays essential roles in a range of biological processes, including cell proliferation, inflammation, and metabolism. In this study, we investigated the effects of a novel synthetic lithocholic acid derivative with vitamin D activity (Dcha-20) on pharmacokinetic gene expression in human induced pluripotent stem cell-derived intestinal organoids. Compared with vitamin D3 treatment, Dcha-20 was found to upregulate the expression and enzyme activity of the drug-metabolizing enzyme CYP3A4, an indicator of intestinal functional maturation. In addition, Dcha-20 specifically increased expression levels of the xenobiotic detoxification enzyme UGT1A and excretion transporter MRP2. These results suggest that Dcha-20 promotes activity of the intrinsic defense system of the intestinal epithelium.

2. [Social Aspects of Euthanasia]

Roberto Germán Zurriaráin Cuad Bioet. 2019 Jan-Apr;30(98):23-34.

This article analyzes the issue of euthanasia, but under a concrete point of view, that of its social implications. It is defended here that euthanasia is not exclusively an individual decision, but has, above all, an important social repercussion. If euthanasia were accepted and legalized, the very nature of the medicine and the physician's own identity would undergo a profound transformation. The doctor-patient relationship based on trust would be broken. Also, if euthanasia were endorsed, it would be encouraged that the human being was not valued for his / her being, but for his capacity to produce. Now, vulnerable, fragile and weak people (dependent, old, sick ...) keep their dignity intact, because we have this because of the simple fact of being born as human beings. All human lives are worth living, however sick and deteriorated their bodies are. To admit the opposite is to enter a spiral where the dignity of the human being would become an object of weighting with respect to another value, which, in a hypothetical conflict could be postponed by another. However, Palliative Care takes into account the social dimension of the end of life of the human being. They take care of the sick human being in its entirety. That is why they are the option most in line with the dignity of the human being at the end of his life.

3. Anti-inflammatory mechanisms of bioactive milk proteins in the intestine of newborns

Dereck E W Chatterton, Duc Ninh Nguyen, Stine Brandt Bering, Per Torp Sangild Int J Biochem Cell Biol. 2013 Aug;45(8):1730-47. doi: 10.1016/j.biocel.2013.04.028. Epub 2013 May 6.

The human newborn infant is susceptible to gut inflammatory disorders. In particular, growth-restricted infants or infants born prematurely may develop a severe form of intestinal inflammation known as necrotizing enterocolitis (NEC), which has a high mortality. Milk provides a multitude of proteins with anti-inflammatory properties and in this review we gather together some recent significant advances regarding the isolation and proteomic identification of these minor constituents of both human and bovine milk. We introduce the process of inflammation, with a focus on the immature gut, and describe how a multitude of milk proteins act against the inflammatory process according to both in vitro and in vivo studies. We highlight the effects of milk proteins such as caseins, and of whey proteins such as alpha-lactalbumin, beta-lactoglobulin, lactoferrin, osteopontin, immunoglobulins, trefoil factors, lactoperoxidase, superoxide dismutase, platelet-activating factor acetylhydrolase, alkaline phosphatase, and growth factors (TGF-β, IGF-I and IGF-II, EGF, HB-EGF). The effects of milk fat globule proteins, such as TLR-2, TLR-4, sCD14 and MFG-E8/lactadherin, are also discussed. Finally, we indicate how milk proteins could be useful for the prophylaxis and therapy of intestinal inflammation in infants and children.