Fmoc-β-cyclopropyl-L-Alanine
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Fmoc-β-cyclopropyl-L-Alanine

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Category
Fmoc-Amino Acids
Catalog number
BAT-005546
CAS number
214750-76-2
Molecular Formula
C21H21NO4
Molecular Weight
351.30
Fmoc-β-cyclopropyl-L-Alanine
IUPAC Name
(2S)-3-cyclopropyl-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acid
Synonyms
Fmoc-Ala(β-cyclopropyl)-OH
Appearance
White to off-white powder
Purity
≥ 99.5% (Chiral HPLC)
Density
1.291g/cm3
Melting Point
159-162 °C
Boiling Point
583.5°C at 760mmHg
Storage
Store at 2-8°C
InChI
InChI=1S/C21H21NO4/c23-20(24)19(11-13-9-10-13)22-21(25)26-12-18-16-7-3-1-5-14(16)15-6-2-4-8-17(15)18/h1-8,13,18-19H,9-12H2,(H,22,25)(H,23,24)/t19-/m0/s1
InChI Key
DRGUEWQZLABTFG-IBGZPJMESA-N
Canonical SMILES
C1CC1CC(C(=O)O)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24

Fmoc-β-cyclopropyl-L-alanine, a non-natural amino acid integral to peptide synthesis, plays a pivotal role in diverse biochemical contexts. Here are the key applications of Fmoc-β-cyclopropyl-L-alanine presented with high perplexity and burstiness:

Peptide Drug Development: In the realm of therapeutic innovation, researchers harness Fmoc-β-cyclopropyl-L-alanine to fortify peptide sequences, enhancing their stability and bioactivity. This strategic modification elevates the pharmacokinetic attributes of peptide drugs, bolstering their resilience to enzymatic degradation. This amino acid is instrumental in crafting therapeutic peptides aimed at combatting prevalent diseases such as cancer, diabetes, and infectious ailments.

Structural Biology: Delving into the intricacies of peptides and proteins, scientists utilize Fmoc-β-cyclopropyl-L-alanine to interrogate structure-activity relationships. By introducing this non-natural amino acid, researchers delve into how conformational constraints impact protein folding and functionality. This knowledge is paramount for unraveling protein dynamics and devising innovative biomolecules that push the boundaries of structural biology.

Chemical Biology: The synthesis of peptide probes for labeling and imaging studies is greatly enriched by the use of Fmoc-β-cyclopropyl-L-alanine. These probes serve as invaluable tools for tracking protein interactions and localization within live cells, offering profound insights into cellular processes. The constrained nature of this amino acid amplifies the creation of highly selective and potent probes, fueling advancements in chemical biology.

Biomaterial Engineering: At the intersection of biomaterials and innovation, Fmoc-β-cyclopropyl-L-alanine emerges as a key player in crafting peptides with enhanced mechanical properties for scaffolds and hydrogels. Tailored peptides engineered with this amino acid facilitate cell adhesion, proliferation, and differentiation, crucial for applications in tissue engineering and regenerative medicine. This utilization underscores the pivotal role of Fmoc-β-cyclopropyl-L-alanine in shaping the landscape of biomaterial innovation.

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