title: Synthesis of cyclically constrained sugar derived α/β- and α/γ-peptides.
abstract: A general approach to enantiopure conformationally constrained sugar derived α/β- and α/γ-peptides has been established. Five-membered ring α/β-peptides were synthesized via formyl C-glycofuranosides, easy available from hexose-derived azido-2-equatorial-OH-glycopyranosides by DAST-promoted ring contraction. By means of a regioselective oxidation with TEMPO at C-6 of hexose-derived 3-azido glycopyranosides as the key step, two- and three-residue α/γ-peptides having a six-membered ring were obtained in good yields and under very simple experimental conditions.
authors.affiliation: Departamento de Química Orgánica, Facultad de Química, Universidad de Sevilla, C/Profesor García González 1, 41012 Sevilla, Spain.
authors.forename: Antonio
authors.initials: A
authors.lastname: Franconetti
authors.forename: Sorel
authors.initials: S
authors.lastname: Jatunov
authors.forename: Pastora
authors.initials: P
authors.lastname: Borrachero
authors.forename: Manuel
authors.initials: M
authors.lastname: Gómez-Guillén
authors.forename: Francisca
authors.initials: F
authors.lastname: Cabrera-Escribano
mesh_terms: D060326:Chemistry Techniques, Synthetic; D006027:Glycosides / Q000737:chemistry*; D006868:Hydrolysis; D010084:Oxidation-Reduction; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D006027:Glycosides; D010455:Peptides