title: Synthesis of Mixed α/β2,2-Peptides by Site-Selective Ring-Opening of Cyclic Quaternary Sulfamidates.
abstract: A method for site- and stereoselective peptide modification using a cyclic sulfamidate scaffold containing peptides is described. A peptide synthesis strategy allowing the rapid generation of mixed α/β-peptides incorporating a sulfamidate residue, derived from 2-methylisoserine, has been generalized. The unique electrophilic nature of this scaffold for nucleophilic substitution at a quaternary center with total inversion of its configuration, which was demonstrated computationally, allows for site-selective conjugation with various nucleophiles, such as anomeric thiocarbohydrates and pyridines. This strategy provides rapid access to complex thioglyco-α/β-conjugates and charged α/β-peptides.
authors.affiliation: Departamento de Química, Centro de Investigación en Síntesis Química. Universidad de La Rioja , C/Madre de Dios, 53, 26006 Logroño, La Rioja, Spain.
authors.forename: Nuria
authors.initials: N
authors.lastname: Mazo
authors.affiliation: Departamento de Química, Centro de Investigación en Síntesis Química. Universidad de La Rioja , C/Madre de Dios, 53, 26006 Logroño, La Rioja, Spain.
authors.forename: Iván
authors.initials: I
authors.lastname: García-González
authors.affiliation: Departamento de Química, Centro de Investigación en Síntesis Química. Universidad de La Rioja , C/Madre de Dios, 53, 26006 Logroño, La Rioja, Spain.
authors.forename: Claudio D
authors.initials: CD
authors.lastname: Navo
authors.affiliation: Departamento de Química, Centro de Investigación en Síntesis Química. Universidad de La Rioja , C/Madre de Dios, 53, 26006 Logroño, La Rioja, Spain.
authors.forename: Francisco
authors.initials: F
authors.lastname: Corzana
authors.affiliation: Departamento de Química, Centro de Investigación en Síntesis Química. Universidad de La Rioja , C/Madre de Dios, 53, 26006 Logroño, La Rioja, Spain.
authors.forename: Gonzalo
authors.initials: G
authors.lastname: Jiménez-Osés
authors.affiliation: Departamento de Química, Centro de Investigación en Síntesis Química. Universidad de La Rioja , C/Madre de Dios, 53, 26006 Logroño, La Rioja, Spain.
authors.forename: Alberto
authors.initials: A
authors.lastname: Avenoza
authors.affiliation: Departamento de Química, Centro de Investigación en Síntesis Química. Universidad de La Rioja , C/Madre de Dios, 53, 26006 Logroño, La Rioja, Spain.
authors.forename: Jesús H
authors.initials: JH
authors.lastname: Busto
authors.affiliation: Departamento de Química, Centro de Investigación en Síntesis Química. Universidad de La Rioja , C/Madre de Dios, 53, 26006 Logroño, La Rioja, Spain.
authors.forename: Jesús M
authors.initials: JM
authors.lastname: Peregrina
mesh_terms: D015394:Molecular Structure; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D013451:Sulfonic Acids / Q000737:chemistry*
chemical_list: D010455:Peptides; D013451:Sulfonic Acids; C005741:sulfamic acid