title: Replacement of Ala by Aib improves structuration and biological stability in thymine-based alpha-nucleopeptides.
abstract: Three thymine-based nucleo-heptapeptides, each containing two nucleo-amino acids and zero, one or four Aib residues, respectively, have been synthesized. A single Aib residue is enough to promote the adoption of a helical structure in our nucleopeptides and to increase significantly their resistance towards enzymatic degradation. The insertion of four Aib residues, out of seven residues in the sequence, affords a rigid, 3(10)-helical nucleopeptide that is substantially unaffected by serum enzymes and is not cytotoxic.
authors.affiliation: Department of Chemistry, University of Padova, 35131 Padova, Italy.
authors.forename: Piero
authors.initials: P
authors.lastname: Geotti-Bianchini
authors.forename: Alessandro
authors.initials: A
authors.lastname: Moretto
authors.forename: Cristina
authors.initials: C
authors.lastname: Peggion
authors.forename: Julien
authors.initials: J
authors.lastname: Beyrath
authors.forename: Alberto
authors.initials: A
authors.lastname: Bianco
authors.forename: Fernando
authors.initials: F
authors.lastname: Formaggio
mesh_terms: D000409:Alanine / Q000737:chemistry*; D000595:Amino Acid Sequence; D000621:Aminoisobutyric Acids / Q000737:chemistry*; D000818:Animals; D045744:Cell Line, Tumor; D015195:Drug Design; D006801:Humans; D006868:Hydrolysis; D051379:Mice; D009842:Oligopeptides / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism* / Q000633:toxicity; D011487:Protein Conformation; D055550:Protein Stability; D013941:Thymine / Q000737:chemistry*
chemical_list: D000621:Aminoisobutyric Acids; D009842:Oligopeptides; C100049:2-aminoisobutyric acid; D000409:Alanine; D013941:Thymine