Fmoc-Ala(CF3)-OH
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Fmoc-Ala(CF3)-OH

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Category
Fluorinated Amino Acids
Catalog number
BAT-008255
CAS number
181128-48-3
Molecular Formula
C19H16F3NO4
Molecular Weight
379.3
IUPAC Name
(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-4,4,4-trifluorobutanoic acid
Synonyms
(S)-Fmoc-2-amino-4,4,4-trifluoro-butyric acid; (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-4,4,4-trifluorobutanoic acid
InChI
InChI=1S/C19H16F3NO4/c20-19(21,22)9-16(17(24)25)23-18(26)27-10-15-13-7-3-1-5-11(13)12-6-2-4-8-14(12)15/h1-8,15-16H,9-10H2,(H,23,26)(H,24,25)/t16-/m0/s1
InChI Key
CHNDOSLXDQUFJI-INIZCTEOSA-N
Canonical SMILES
C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)NC(CC(F)(F)F)C(=O)O

Fmoc-Ala(CF3)-OH, a derivative of alanine, utilized in solid-phase peptide synthesis (SPPS), boasts versatility in a myriad of research and industrial settings. Here are the key applications of this compound, presented with elevated levels of perplexity and burstiness:

Peptide Synthesis: Within SPPS, Fmoc-Ala(CF3)-OH plays a pivotal role in incorporating trifluoromethyl-substituted alanine into peptides. This modification serves to bolster peptide stability and hydrophobicity, rendering them more impervious to enzymatic breakdown. Consequently, it emerges as a valuable asset in crafting peptide-based medicines with enhanced pharmacokinetic attributes.

Structural Biology: In the realm of structural biology, Fmoc-Ala(CF3)-OH finds purpose in interrogating protein folding dynamics and molecular interactions. Through the incorporation of the trifluoromethyl group, alterations to protein conformation and stability can be induced. These changes offer illuminating glimpses into folding mechanisms and factors governing protein stabilization, pivotal for unlocking the mysteries of protein functionality and formulating stable protein structures.

Material Science: Delving into material science, Fmoc-Ala(CF3)-OH contributes to the realm of biomaterial innovation. Peptides featuring trifluoromethyl-substituted alanine hold the key to crafting materials endowed with distinctive traits like heightened hydrophobicity and increased thermal resilience. These materials find applications across diverse fields such as drug delivery systems, bioengineering, and the design of functional coatings, heralding innovative solutions for various industrial challenges.

Chemical Biology: Within the realm of chemical biology, Fmoc-Ala(CF3)-OH emerges as a potent tool for probing intricate protein-protein and protein-ligand interactions. By integrating this modified amino acid into peptides or proteins, researchers can explore the impact of the trifluoromethyl group on binding affinities and interaction kinetics. This exploration can pave the way for identifying novel therapeutic targets and formulating innovative inhibitors, driving forward the frontiers of chemical biology research.

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