Boc-β-cyclohexyl-D-alanine
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Boc-β-cyclohexyl-D-alanine

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Category
BOC-Amino Acids
Catalog number
BAT-007185
CAS number
127095-92-5
Molecular Formula
C14H25NO4
Molecular Weight
271.35
Boc-β-cyclohexyl-D-alanine
IUPAC Name
(2R)-3-cyclohexyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
Synonyms
Boc-D-Cha-OH; Boc-3-cyclohexyl-D-alanine; Boc D Cha OH
Related CAS
198470-07-4 (dicyclohexylammonium salt)
Appearance
White or off-white solid
Purity
≥ 99% (Chiral HPLC)
Density
1.083 g/cm3
Melting Point
64-67 °C
Boiling Point
420.4°C at 760 mmHg
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-/m1/s1
InChI Key
MSZQAQJBXGTSHP-LLVKDONJSA-N
Canonical SMILES
CC(C)(C)OC(=O)NC(CC1CCCCC1)C(=O)O

Boc-β-cyclohexyl-D-alanine dicyclohexylammonium salt, a chemical reagent commonly employed in peptide synthesis and organic chemistry, serves a multitude of purposes. Here are four key applications presented with high perplexity and burstiness:

Peptide Synthesis: Serving as a fundamental element in peptide assembly, this compound bestows stability and protection to amino acids throughout coupling reactions. The Boc group acts as a shield for the amino functionality, thwarting undesired side reactions. When required, the Boc group can be selectively cleaved under acidic conditions, enabling seamless elongation of the peptide chain.

Drug Design: In the realm of medicinal chemistry, Boc-β-cyclohexyl-D-alanine dicyclohexylammonium salt plays a pivotal role in crafting peptide-based drug candidates. The β-cyclohexyl group enhances the lipophilicity and stability of peptide drugs, augmenting their pharmacokinetic characteristics. This makes it a valuable asset for formulating therapeutic peptides with improved bioavailability and resilience against enzymatic degradation.

Enzyme Inhibition Studies: Researchers leverage this compound to design and synthesize inhibitors targeting a diverse array of enzymes. Incorporating it into peptide sequences facilitates the exploration of enzyme-substrate interactions and binding affinities. This investigation is essential for deciphering enzyme mechanisms and pinpointing potential drug targets of interest.

Protein-Protein Interaction Studies: Boc-β-cyclohexyl-D-alanine dicyclohexylammonium salt facilitates the development of peptide mimetics capable of modulating protein-protein interactions. By integrating this motif into synthetic peptides, scientists can delve into the formation of protein complexes and unearth molecules that can disrupt or stabilize these interactions. This research is instrumental in uncovering innovative therapeutic strategies for diseases associated with aberrant protein interactions.

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