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


  • We are grateful to Dr. O. V. Shishkin for the X-ray diffractional analysis and Dr. M. Berditsch for help with antimicrobial assays. This work was supported by Enamine Ltd. and by DAAD (A.N.T.).


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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.