The nitroxide spin-labelled beta-2,3-cyclic amino acid POAC was synthesized, resolved and its absolute confi guration assigned (K. Wright et al., Tetrahedron, 2008, 64, 4416-4426) 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;FRANCO, LORENZO;
2008
Abstract
The nitroxide spin-labelled beta-2,3-cyclic amino acid POAC was synthesized, resolved and its absolute confi guration assigned (K. Wright et al., Tetrahedron, 2008, 64, 4416-4426) 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.File in questo prodotto:
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