The first photoinduced intramolecular macrocyclization reaction in a helical peptide, containing a Bpa and a Met residue incorporated one on top of the other after a complete turn of the helix (see figure), has been performed. The photochemical remote functionalization and subsequent intramolecular cross-linking are strictly regioselective, involving exclusively the original Met side-chain ε-CH3 group and generating two diastereomeric macrocyclized peptides.
Photoinduced Intramolecular Macrocyclization Reaction between a Bpa and a Met Residue in a Helical Peptide: 3D Structures of the Diastereomeric Products
MORETTO, ALESSANDRO;FORMAGGIO, FERNANDO;TONIOLO, CLAUDIO
2009
Abstract
The first photoinduced intramolecular macrocyclization reaction in a helical peptide, containing a Bpa and a Met residue incorporated one on top of the other after a complete turn of the helix (see figure), has been performed. The photochemical remote functionalization and subsequent intramolecular cross-linking are strictly regioselective, involving exclusively the original Met side-chain ε-CH3 group and generating two diastereomeric macrocyclized peptides.File in questo prodotto:
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