Fmoc-R-(Me)Ala(3-F3)-OH
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Fmoc-R-(Me)Ala(3-F3)-OH

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Category
Fluorinated Amino Acids
Catalog number
BAT-008539
CAS number
1932361-33-5
Molecular Formula
C19H16F3NO4
Molecular Weight
379.3
IUPAC Name
(2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3,3,3-trifluoro-2-methylpropanoic acid
Synonyms
Fmoc-aMeAla(F3)-OH; (R)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3,3,3-trifluoro-2-methylpropanoic acid
Density
1.4±0.1 g/cm3
Boiling Point
527.8±50.0 °C at 760 mmHg
InChI
InChI=1S/C19H16F3NO4/c1-18(16(24)25,19(20,21)22)23-17(26)27-10-15-13-8-4-2-6-11(13)12-7-3-5-9-14(12)15/h2-9,15H,10H2,1H3,(H,23,26)(H,24,25)/t18-/m1/s1
InChI Key
WDBDMOCINHCAEN-GOSISDBHSA-N
Canonical SMILES
CC(C(=O)O)(C(F)(F)F)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13

Fmoc-R-(Me)Ala(3-F3)-OH, a specialized amino acid derivative utilized in peptide synthesis and biochemical research, serves as a versatile tool in various applications. Here are the key applications presented with high perplexity and burstiness:

Peptide Synthesis: In the realm of solid-phase peptide synthesis, Fmoc-R-(Me)Ala(3-F3)-OH emerges as a pivotal building block. Its distinctive structure facilitates the integration of modified alanine residues capable of modulating the peptide's conformation and biological functions. This property renders it invaluable for crafting peptides endowed with specific characteristics and functionalities, unlocking a realm of design possibilities to researchers.

Protein Engineering: Delving into protein modification, researchers leverage Fmoc-R-(Me)Ala(3-F3)-OH to introduce non-natural amino acids into proteins. This intervention allows for the exploration of side-chain alterations' impacts on protein folding, stability, and activity. Such modifications play a critical role in the development of proteins with heightened or novel functionalities, particularly pertinent in the realm of therapeutic innovations and applications.

Drug Discovery: At the frontier of pharmaceutical investigations, Fmoc-R-(Me)Ala(3-F3)-OH plays a vital role in the creation of peptide-based drug candidates. By incorporating this amino acid derivative into therapeutic peptides, scientists bolster binding affinity, stability, and resistance to enzymatic breakdown. This strategic approach amplifies the design efficacy of peptide drugs targeting specific receptors or enzymes, fueling advancements in precise drug delivery mechanisms.

Biophysical Studies: Unveiling the intricacies of peptide interactions and folding mechanisms, Fmoc-R-(Me)Ala(3-F3)-OH emerges as a key player in biophysical analyses. Its fluorinated side chain holds promise in spectroscopic inquiries, such as NMR or fluorescence, enabling in-depth scrutiny of peptide conformation and dynamics. This interdisciplinary approach sheds light on the fundamental tenets of protein structure and function, offering a nuanced understanding of biological processes at the molecular level.

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