The nitroxide spin-labelled beta-2,3-cyclic amino acid POAC was synthesized, resolved and its absolute confi guration assigned in order to be used as a spin-probe to evaluate the 12-helical beta-peptide secondary structure. A series of beta-hexapeptides, Boc-ACPC-POAC-POAC-ACPC-ACPC-ACPC-OMe, Boc-ACPC-POAC-ACPC-POAC-ACPC-ACPC-OMe, Boc-ACPC-POAC-ACPC-ACPC-POAC-ACPC-OMe, and Boc-ACPC-POAC-ACPC-ACPC-ACPC-POAC-OMe, based on the (3R,4R)-POAC enantiomer, combined with (1S,2S)-ACPC for confi gurational homogeneity of the amino acid components, was designed.
Synthesis and conformational analysis of doubly spin-labelled beta-peptides based on the nitroxide bearing POAC residue
TONIOLO, CLAUDIO;FORMAGGIO, FERNANDO;TOFFOLETTI, ANTONIO;
2008
Abstract
The nitroxide spin-labelled beta-2,3-cyclic amino acid POAC was synthesized, resolved and its absolute confi guration assigned in order to be used as a spin-probe to evaluate the 12-helical beta-peptide secondary structure. A series of beta-hexapeptides, Boc-ACPC-POAC-POAC-ACPC-ACPC-ACPC-OMe, Boc-ACPC-POAC-ACPC-POAC-ACPC-ACPC-OMe, Boc-ACPC-POAC-ACPC-ACPC-POAC-ACPC-OMe, and Boc-ACPC-POAC-ACPC-ACPC-ACPC-POAC-OMe, based on the (3R,4R)-POAC enantiomer, combined with (1S,2S)-ACPC for confi gurational homogeneity of the amino acid components, was designed.
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