Fmoc-β-cyclohexyl-D-alanine
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Fmoc-β-cyclohexyl-D-alanine

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Category
Fmoc-Amino Acids
Catalog number
BAT-005544
CAS number
144701-25-7
Molecular Formula
C24H27NO4
Molecular Weight
393.48
Fmoc-β-cyclohexyl-D-alanine
IUPAC Name
(2R)-3-cyclohexyl-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acid
Synonyms
Fmoc-D-Cha-OH; Fmoc-3-cyclohexyl-D-alanine
Appearance
White powder
Purity
≥ 98% (HPLC)
Density
1.2±0.1 g/cm3
Boiling Point
610.5±38.0 °C
Storage
Store at 2-8°C
InChI
InChI=1S/C24H27NO4/c26-23(27)22(14-16-8-2-1-3-9-16)25-24(28)29-15-21-19-12-6-4-10-17(19)18-11-5-7-13-20(18)21/h4-7,10-13,16,21-22H,1-3,8-9,14-15H2,(H,25,28)(H,26,27)/t22-/m1/s1
InChI Key
HIJAUEZBPWTKIV-JOCHJYFZSA-N
Canonical SMILES
C1CCC(CC1)CC(C(=O)O)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24

Fmoc-β-cyclohexyl-D-alanine, a specialized amino acid derivative crucial in peptide synthesis, finds diverse applications in the realm of biochemistry. Here are the key applications presented with high perplexity and burstiness:

Peptide Synthesis: Embedding Fmoc-β-cyclohexyl-D-alanine within synthetic peptides elevates their structural integrity and biological potency. The introduction of the bulky cyclohexyl group impacts the peptide's folding dynamics and its interactions with target molecules. This unique amino acid derivative plays a pivotal role in crafting peptides with heightened resilience against enzymatic breakdown, showcasing its utility in peptide design for various applications.

Drug Design: In the realm of drug discovery, Fmoc-β-cyclohexyl-D-alanine serves as a cornerstone in developing peptide-based drug candidates with optimized pharmacokinetic attributes. Leveraging the distinctive structure of this amino acid derivative enhances the binding affinity and specificity of peptides towards their molecular targets, paving the way for the creation of more efficacious therapeutic agents with minimized adverse effects. This innovative approach reshapes the landscape of pharmaceutical research and development.

Protein-Protein Interaction Studies: Employed in elucidating protein-protein interactions, Fmoc-β-cyclohexyl-D-alanine is strategically incorporated into peptide mimetics. These engineered peptides have the potential to perturb or stabilize interactions between proteins, offering valuable insights into their functional roles within biological processes. This application not only deepens our understanding of molecular interactions but also identifies novel avenues for drug target discovery, pushing the boundaries of biotechnological research.

Bioconjugation: Facilitating bioconjugation techniques, Fmoc-β-cyclohexyl-D-alanine enables the coupling of peptides to diverse biomolecules like antibodies or nanoparticles. The resultant conjugates find utility in targeted drug delivery, diagnostic assays, and imaging modalities, enhancing the precision and efficacy of therapeutic and diagnostic interventions. This innovative approach in bioconjugation opens up new possibilities for tailored biomedical applications, propelling advancements in precision medicine and diagnostics.

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