Fluorinated Building Blocks

Fluorinated Building Blocks Produce Molecules with Enhanced Physiological Activities

The substitution of the fluorine in place of hydrogen in building blocks, such as amino acids, has produced molecules with enhanced physiological activities (1-2). Some of these are antibacterial, antihypertensive and antitumoral (3). One reason for the enhanced activity is that fluorine forms a strong covalent bond with a carbon atom, which in peptides creates hyper-stable protein folds that render fluoro amino acid-containing peptides resistant to metabolic transformation (2, 4). The electronegativity of fluorine affects the pH of the neighboring groups, which in turn causes an overall change in the stability and reactivity of a molecule (2).

Selected Listing of Fluorinated Amino Acids

Product DescriptionSize Cat #
Fmoc-3,4-difluoro-L-phenylalanine 1 g26719-F1
Fmoc-5-fluoro-DL-tryptophan 100 mg 26171-F01
Fmoc-5-fluoro-DL-tryptophan 1 g 26171-F1
Fmoc-3-fluoro-DL-tyrosine 100 mg26085-F01
Fmoc-4-fluoro-L-phenylglycine 1g AS-26255-F1
Fmoc-trans-4-Fluoro-L-proline 1g AS-60438-F1
Fmoc-4-fluoro-L-phenylalanine 1 g 23379

1. Welch, JT. Tetrahedron 43, 3123 (1987).
2. Sutherland, A. and CL. Willis. Nat. Prod. Rep. 17, 621 (2000).
3. Davis, FA. et al. J. Org. Chem. 64, 6931 (1999).
4. Yoder, NC. And K. Kumar. Chem. Soc. Rev. 31, 335 (2002).