{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,3,13]],"date-time":"2026-03-13T07:29:10Z","timestamp":1773386950123,"version":"3.50.1"},"reference-count":33,"publisher":"Wiley","issue":"9","license":[{"start":{"date-parts":[[2007,8,13]],"date-time":"2007-08-13T00:00:00Z","timestamp":1186963200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Journal of Peptide Science"],"published-print":{"date-parts":[[2007,9]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>The conformation, alignment and dynamic behavior of membrane\u2010bound peptides is readily accessible by solid\u2010state <jats:sup>19<\/jats:sup>F\u2010NMR spectroscopy, but it has been difficult to incorporate suitable <jats:sup>19<\/jats:sup>F\u2010labelled amino acids into synthetic peptides. To avoid the drawbacks of previously used labels, we have rationally designed and synthesized a novel amino acid that suits all theoretical and practical requirements for peptide synthesis and subsequent <jats:sup>19<\/jats:sup>F\u2010NMR structure analysis [Mikhailiuk <jats:italic>et. al,<\/jats:italic> Angew. Chem. 2006, 118, 5787\u20135789]. The enantiomerically pure <jats:sc>L<\/jats:sc>\u2010form of 3\u2010(trifluoromethyl)bicyclopent\u2010[1.1.1]\u20101\u2010ylglycine (CF<jats:sub>3<\/jats:sub>\u2010Bpg) carries a CF<jats:sub>3<\/jats:sub> group that is rigidly attached to the peptide backbone and does not racemize during peptide synthesis. It could be demonstrated for several different peptides that their biological activity is usually not affected by a single label, nor the conformation, as monitored by circular dichroism. Here, we carry out a more detailed structure analysis to evaluate the potential and reliability of CF<jats:sub>3<\/jats:sub>\u2010Bpg for solid\u2010state NMR, using the well\u2010known \u03b1\u2010helical antimicrobial peptide PGLa as a test case. We have collected several orientational constraints from the anisotropic <jats:sup>19<\/jats:sup>F\uf8ff<jats:sup>19<\/jats:sup>F dipolar couplings of CF<jats:sub>3<\/jats:sub>\u2010Bpg in various positions of PGLa embedded in lipid bilayers. These resulting structural parameters are then compared with those previously determined from 4\u2010CF<jats:sub>3<\/jats:sub>\u2010phenylglycine and 3,3,3\u2010<jats:italic>d<\/jats:italic><jats:sub>3<\/jats:sub>\u2010alanine labels on the same peptide. The analysis confirms that CF<jats:sub>3<\/jats:sub>\u2010Bpg does not perturb the \u03b1\u2010helical conformation of PGLa. Likewise, the helix alignment is shown to follow the established concentration\u2010dependent pattern in realigning from a surface\u2010bound S\u2010state to an obliquely tilted T\u2010state. Hence, the advantages of CF<jats:sub>3<\/jats:sub>\u2010Bpg over all previously used <jats:sup>19<\/jats:sup>F\u2010labeled side chains are evident, as they combine ease of chemical incorporation and peptide purification with high NMR sensitivity and absent background signals, allowing a straightforward analysis of the dipolar splittings with no need for chemical shift referencing without any ambiguity in the sign of the couplings. Copyright \u00a9 2007 European Peptide Society and John Wiley &amp; Sons, Ltd.<\/jats:p>","DOI":"10.1002\/psc.854","type":"journal-article","created":{"date-parts":[[2007,8,13]],"date-time":"2007-08-13T09:46:26Z","timestamp":1186998386000},"page":"614-623","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":54,"title":["Evaluating the amino acid CF<sub>3<\/sub>\u2010bicyclopentylglycine as a new label for solid\u2010state <sup>19<\/sup>F\u2010NMR structure analysis of membrane\u2010bound peptides"],"prefix":"10.1002","volume":"13","author":[{"given":"Sergii","family":"Afonin","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Pavel K.","family":"Mikhailiuk","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Igor 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