175548-85-3Relevant academic research and scientific papers
Chemoenzymatic synthesis of each enantiomer of orthogonally protected 4,4-difluoroglutamic acid: A candidate monomer for chiral Bronsted acid peptide-based catalysts
Li, Yang,Miller, Scott J.
, p. 9785 - 9791 (2012/01/05)
We have accomplished an asymmetric synthesis of each enantiomer of 4,4-difluoroglutamic acid. This α-amino acid has been of interest in medicinal chemistry circles. Key features of the synthesis include highly scalable procedures, a Reformatsky-based coupling reaction, and straightforward functional group manipulations to make the parent amino acid. Enantioenrichment derives from an enzymatic resolution of the synthetic material. Conversion of the optically enriched compounds to orthogonally protected forms allows for the selective formation of peptide bonds. 4,4-Difluoroglutamic acid, in a suitably protected form, is also shown to exhibit enhanced catalytic activity in both an oxidation reaction and a reduction reaction, in comparison to the analogous glutamic acid derivative.
Facile synthesis of DL-4,4-difluoroornithine, DL-4,4-difluoroglutamine, and γ-DL-4,4-difluoroglutamyl-containing peptides: Regiospecific addition of nucleophiles to N-Cbz-di-tert-butyl-DL-4,4-difluoroglutamate
Tsukamoto,Coward
, p. 2497 - 2500 (2007/10/03)
The reaction of several nucleophiles with N-Cbz-protected di-tert-butyl-DL-4,4-difluoroglutamate was investigated as an approach to the synthesis of various fluorinated amino acids and peptides. The γ-carboxyl group is highly activated by the two adjacent fluorine atoms, and nucleophilic reactions occurred exclusively at that carbonyl carbon. Further transformations of the reaction products resulted in the synthesis of DL-4,4-difluoroornithine, DL-4,4-difluoroglutamine, and γ-DL-4,4-difluoroglutamyl-containing dipeptides.
