title: A convenient asymmetric synthesis of a beta-amino ester with additional functionalization as a precursor for peptide nucleic acid (PNA) monomers.
abstract: We report the asymmetric synthesis of di-3-pentyl (3S,alphaS,7E)-3-N-benzyl-N-alpha-methylbenzylamino-dec-7-enedioate (9), which contains the correct functionalization to produce delta-amino acid derivatives to be used as monomers for Peptide Nucleic Acid (PNA) formation With this aim, thymine-pentanoic acid 15 and some of its ester derivatives were obtained, their reactivity was studied and the noteworthy ethyl ester 12 was quantitatively produced by transesterification of methyl ester 11, thus paving the way for the synthesis of the thymine-containing amino ester IV, which has been designed as a building block for a Nucleic-Acid analog with a chiral, flexible peptide backbone.
authors.affiliation: Departamento de Química Orgánica, Universidad de Salamanca, Plaza de los Caídos 1-5, 37008, Salamanca, Spain. nmg@usal.es
authors.forename: Narciso M
authors.initials: NM
authors.lastname: Garrido
authors.forename: David
authors.initials: D
authors.lastname: Díez
authors.forename: Sara H
authors.initials: SH
authors.lastname: Domínguez
authors.forename: M Rosa
authors.initials: MR
authors.lastname: Sánchez
authors.forename: Mercedes
authors.initials: M
authors.lastname: García
authors.forename: Julio G
authors.initials: JG
authors.lastname: Urones
mesh_terms: D000596:Amino Acids / Q000737:chemistry; D004951:Esterification; D020135:Peptide Nucleic Acids / Q000138:chemical synthesis* / Q000737:chemistry*; D013941:Thymine / Q000031:analogs & derivatives / Q000737:chemistry
chemical_list: D000596:Amino Acids; D020135:Peptide Nucleic Acids; D013941:Thymine