Boc-β-cyclohexyl-L-alanine
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Boc-β-cyclohexyl-L-alanine

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Boc-β-cyclohexyl-L-alanine, is an Alanine derivative, that can be used as an intermediate in the synthesis of pharmaceutical and biologically active compounds, including inhibitors. It is used in the synthesis of a novel class of piperidine or morpholine-based renin inhibitors, and also for the preparation of Remikiren.

Category
BOC-Amino Acids
Catalog number
BAT-007932
CAS number
37736-82-6
Molecular Formula
C14H25NO4
Molecular Weight
271.35
Boc-β-cyclohexyl-L-alanine
IUPAC Name
(2S)-3-cyclohexyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
Synonyms
Boc-L-Cha-OH; Boc-3-cyclohexyl-L-alanine; (S)-2-tert-Butoxycarbonylamino-3-cyclohexyl-propionic acid; Boc-Cha-OH; BOC-BETA-CYCLOHEXYL-ALA-OH; Boc-L-cyclohexylalanine; (S)-2-(tert-butoxycarbonylamino)-3-cyclohexylpropanoic acid; Cyclohexanepropanoic acid, a-[[(1,1-dimethylethoxy)carbonyl]amino]-,(aS)-; N-BOC-b-cyclohexylalanine; AK-76930; Boc-3-cyclohexyl-L-alanine; N-BOC-beta-cyclohexylalanine; Boc L Cha OH
Appearance
White crystalline powder
Purity
99%
Density
1.083±0.06 g/cm3 (Predicted)
Boiling Point
420.4±28.0 °C (Predicted)
Storage
Store at 2-8 °C
InChI
InChI=1S/C14H25NO4/c1-14(2,3)19-13(18)15-11(12(16)17)9-10-7-5-4-6-8-10/h10-11H,4-9H2,1-3H3,(H,15,18)(H,16,17)/t11-/m0/s1
InChI Key
MSZQAQJBXGTSHP-NSHDSACASA-N
Canonical SMILES
CC(C)(C)OC(=O)NC(CC1CCCCC1)C(=O)O

Boc-β-cyclohexyl-L-alanine, a versatile chemical compound, finds widespread use in organic synthesis and peptide chemistry. Here are the key applications presented with high perplexity and burstiness:

Peptide Synthesis: Indispensable in peptide synthesis, Boc-β-cyclohexyl-L-alanine serves as a foundational building block facilitating the creation of peptides. The bulky cyclohexyl group plays a vital role in safeguarding the amino group during coupling reactions ensuring a methodical and controlled synthesis process that culminates in the production of high-purity peptide products.

Drug Design: In the realm of medicinal chemistry, the incorporation of Boc-β-cyclohexyl-L-alanine into drug molecules elevates their pharmacological prowess. By enhancing hydrophobic interactions with their targets, this compound can boost the binding affinity and efficacy of drugs. Its addition becomes a crucial element in tailoring peptide-based therapeutics for optimal performance.

Protease Inhibitors: Delving into the synthesis of protease inhibitors, Boc-β-cyclohexyl-L-alanine emerges as a key player in impeding protease activity a pivotal task in drug development for conditions like cancer and viral infections. The presence of the cyclohexyl group introduces steric bulk potentially heightening specificity towards the target protease thereby advancing our ability to create tailored treatments.

Structural Studies: Within structural biology researchers leverage, Boc-β-cyclohexyl-L-alanine to explore protein-ligand interactions and unravel molecular intricacies. By integrating this compound into peptides or small molecules, scientists gain insights into how structural alterations impact binding and activity. This comprehension serves as a cornerstone for rational drug design and deepening our understanding of protein functionality at a molecular level.

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