Catalog Number
ACM198560439
Product Name
Fmoc-3,4-difluoro-L-phenylalanine
Description
Fmoc-3,4-difluoro-L-phenylalanine is a non-natural amino acid that contains a substituted phenylalanine residue, which is characterized by the presence of two fluorine atoms on the 3 and 4 positions of the aromatic ring. This modification enhances the lipophilicity of the phenylalanine residue and provides unique steric and electronic properties compared to the natural phenylalanine. Fmoc-3,4-difluoro-L-phenylalanine is widely used in peptide synthesis, pharmaceuticals, and materials science due to its ability to form stable secondary structures, such as helices and beta-turns, in peptides and proteins.
Synonyms
N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-3,4-difluoro-L-phenylalanine, Fmoc-D-phe(3,4-F2)-OH, Fmoc-Phe(3,4-F2)-OH, Fmoc-L-3,4-Difluorophenylalanine
IUPAC Name
(2S)-3-(3,4-difluorophenyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acid
Molecular Formula
C24H19F2NO4
Canonical SMILES
C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)NC(CC4=CC(=C(C=C4)F)F)C(=O)O
InChI
1S/C24H19F2NO4/c25-20-10-9-14(11-21(20)26)12-22(23(28)29)27-24(30)31-13-19-17-7-3-1-5-15(17)16-6-2-4-8-18(16)19/h1-11,19,22H,12-13H2,(H,27,30)(H,28,29)/t22-/m0/s1
InChI Key
IHSYIDJNVXPQRM-QFIPXVFZSA-N
Boiling Point
622.7±55.0 ℃at 760 mmHg
Application
Fmoc-3,4-difluoro-L-phenylalanine has been widely used in various scientific experiments. It is commonly used in peptide synthesis to enhance the bioactivity and stability of peptides. Fmoc-3,4-difluoro-L-phenylalanine-containing peptides have also been used in drug discovery to develop novel therapeutics. Additionally, Fmoc-3,4-difluoro-L-phenylalanine has been utilized in materials science to create novel hydrogels, coatings, and other materials.
Type
Unusual Amino Acids, Analogs of Phenylalanine and Tyrosine
Vapor Pressure
0.0±1.9 mmHg at 25℃
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