title: Practical synthesis of novel phosphonopeptides containing Aib(P).
abstract: Practical and convenient method for the synthesis of novel phosphonopeptides 8a-h and 10a-f incorporating the quaternary α-aminophosphonate 6 is reported. The target compounds were prepared in moderate to good yield based on the preparation of the quaternary α-aminophosphonate 6 followed by the formation of the α-bromoamide 7 and subsequent nucleophilic substitution reaction with several amines or by peptide bond formation with several amino acids and with the quaternary α-aminophosphonate 6, using isobutyl chloroformate as activating agent under racemization-free condition.
authors.affiliation: Centro de Investigaciones Químicas CIQ-IICBA, Universidad Autónoma del Estado de Morelos, Av. Universidad 1001, 62209, Cuernavaca, Morelos, Mexico.
authors.forename: Juan Manuel Junior
authors.initials: JM
authors.lastname: Cervera-Villanueva
authors.affiliation: Secretaría Académica, Universidad Autónoma del Estado de Morelos, Av. Universidad 1001, 62209, Cuernavaca, Morelos, Mexico.
authors.forename: José Luis
authors.initials: JL
authors.lastname: Viveros-Ceballos
authors.affiliation: Centro de Investigaciones Químicas CIQ-IICBA, Universidad Autónoma del Estado de Morelos, Av. Universidad 1001, 62209, Cuernavaca, Morelos, Mexico.
authors.forename: Irma
authors.initials: I
authors.lastname: Linzaga-Elizalde
authors.affiliation: Centro de Investigaciones Químicas CIQ-IICBA, Universidad Autónoma del Estado de Morelos, Av. Universidad 1001, 62209, Cuernavaca, Morelos, Mexico.
authors.forename: Mario
authors.initials: M
authors.lastname: Ordóñez
mesh_terms: D000215:Acylation; D000621:Aminoisobutyric Acids / Q000737:chemistry*; D002384:Catalysis; D005561:Formates / Q000737:chemistry; D006020:Glycopeptides / Q000138:chemical synthesis*; D006865:Hydrogenation; D006868:Hydrolysis; D063065:Organophosphonates / Q000138:chemical synthesis*; D012997:Solvents / Q000737:chemistry
chemical_list: D000621:Aminoisobutyric Acids; D005561:Formates; D006020:Glycopeptides; D063065:Organophosphonates; D012997:Solvents; C100049:2-aminoisobutyric acid
keywords: phosphonopeptides; quaternary α-aminophosphonates; three-component reaction