Synthesis and physical chemical properties of 2-amino-4-(trifluoromethoxy)butanoic acid - a CF 3 O-containing analogue of natural lipophilic amino acids

2-Amino-2-(trifluoromethoxy)butanoic acid (O-trifluoromethyl homoserine) was synthesized as a racemate and in both enantiomeric forms. The measured pK and log D values establish the compound as a promising analogue of natural aliphatic amino acids.

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2017-01, Vol.15 (3), p.672-679
Main Authors: Kondratov, Ivan S, Logvinenko, Ivan G, Tolmachova, Nataliya A, Morev, Roman N, Kliachyna, Maria A, Clausen, Florian, Daniliuc, Constantin G, Haufe, Günter
Format: Article
Language:English
Subjects:
Amino Acids - chemical synthesis
Amino Acids - chemistry
Butyrates - chemical synthesis
Butyrates - chemistry
Chemistry, Physical
Hydrocarbons, Fluorinated - chemistry
Hydrophobic and Hydrophilic Interactions
Models, Molecular
Molecular Structure
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Summary:2-Amino-2-(trifluoromethoxy)butanoic acid (O-trifluoromethyl homoserine) was synthesized as a racemate and in both enantiomeric forms. The measured pK and log D values establish the compound as a promising analogue of natural aliphatic amino acids.
ISSN:1477-0520
1477-0539
DOI:10.1039/C6OB02436J