A convenient asymmetric synthesis of a beta-amino ester with additional functionalization as a precursor for peptide nucleic acid (PNA) monomers.
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.
Garrido
Narciso M
NM
Departamento de Química Orgánica, Universidad de Salamanca, Plaza de los Caídos 1-5, 37008, Salamanca, Spain. nmg@usal.es
Díez
David
D
Domínguez
Sara H
SH
Sánchez
M Rosa
MR
García
Mercedes
M
Urones
Julio G
JG
D000596:Amino Acids / Q000737:chemistry; D004951:Esterification; D020135:Peptide Nucleic Acids / Q000138:chemical synthesis* / Q000737:chemistry*; D013941:Thymine / Q000031:analogs & derivatives / Q000737:chemistry
D000596:Amino Acids; D020135:Peptide Nucleic Acids; D013941:Thymine