Trifluoroacetyl group

Blue- marked trifluoroacetyl group in (from top to bottom) trifluoroacetic acid, N -trifluoroacetyl-protected glycine and N -trifluoroacetyl-protected amino acid tert-butyl esters.

The trifluoroacetyl group is briefly referred to as the TFA radical in organic chemistry . It is often used as a protective group within organic synthesis strategies to prevent undesired conversions of free amines . The main area of ​​application is the construction of peptides from protected amino acids .

use

The trifluoroacetyl group can be easily introduced into a molecule to protect an amine by reacting the amine with trifluoroacetic anhydride in anhydrous trifluoroacetic acid . The protecting group is stable under many chemical reaction conditions, but is easily attacked by bases. Dilute caustic soda , barium hydroxide solution or ammonia solution is used for deprotection.

Because of their high volatility, N -trifluoroacetyl-protected amino acid or peptide esters are important for gas chromatographic separations.

Individual evidence

1. ↑ Hans-Dieter Jakubke, Hans Jeschkeit: amino acids, peptides, proteins , Verlag Chemie, Weinheim, 128-129, 1982, ISBN 3-527-25892-2 .
2. ↑ Otto-Albrecht Neumüller (Ed.): Römpps Chemie-Lexikon. Volume 6: T-Z. 8th revised and expanded edition. Franckh'sche Verlagshandlung, Stuttgart 1988, ISBN 3-440-04516-1 , p. 4349.