A ¹⁹F NMR Label to Substitute Polar Amino Acids in Peptides: A CF₃-Substituted Analogue of Serine and Threonine

Rigid & polar: The cyclobutane scaffold was used to design the first polar nonperturbing rigid CF₃-substituted amino acid (left in picture) suitable for replacing the serine/threonine residues in peptides. This amino acid imitates the geometry, structure, and function of serine and threonine, but in contrast to those, it can be used in structural studies of membrane-active Ser/Thr-containing peptides by solid-state ¹⁹F NMR spectroscopy

Tkachenko A. N.; Mykhailiuk P. K.; Afonin S.; Radchenko D. S.; Kubyshkin V. S.; Ulrich A. S.; Komarov I. V.
Angew. Chem. Int. Ed. 2013, 52 (5), 1486-1489
DOI: 10.1002/anie.201208069