Molecules 2006, 11(6), 435-443; doi:10.3390/11060435
Article

A Convenient Asymmetric Synthesis of a β-amino Ester with Additional Functionalization as a Precursor for Peptide Nucleic Acid (PNA) Monomers

Narciso M. Garrido* email, David Díez, Sara H. Domínguez, M. Rosa Sánchez, Mercedes García and Julio G. Urones
Departamento de Química Orgánica, Universidad de Salamanca, Plaza de los Caídos 1-5, 37008, Salamanca, Spain
* Author to whom correspondence should be addressed.
Received: 8 June 2006; in revised form: 13 June 2006 / Accepted: 15 June 2006 / Published: 21 June 2006
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Abstract: We report the asymmetric synthesis of di-3-pentyl (3S,αS,7E)-3-N-benzyl-N- α-methylbenzylamino-dec-7-enedioate (9), which contains the correct functionalization to produce δ-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
Keywords: Peptide nucleic acids (PNA); thymine derivatives; transesterification; asymmetric synthesis; β-amino acids.

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MDPI and ACS Style

Garrido, N.M.; Díez, D.; Domínguez, S.H.; Sánchez, M.R.; García, M.; Urones, J.G. A Convenient Asymmetric Synthesis of a β-amino Ester with Additional Functionalization as a Precursor for Peptide Nucleic Acid (PNA) Monomers. Molecules 2006, 11, 435-443.

AMA Style

Garrido NM, Díez D, Domínguez SH, Sánchez MR, García M, Urones JG. A Convenient Asymmetric Synthesis of a β-amino Ester with Additional Functionalization as a Precursor for Peptide Nucleic Acid (PNA) Monomers. Molecules. 2006; 11(6):435-443.

Chicago/Turabian Style

Garrido, Narciso M.; Díez, David; Domínguez, Sara H.; Sánchez, M. R.; García, Mercedes; Urones, Julio G. 2006. "A Convenient Asymmetric Synthesis of a β-amino Ester with Additional Functionalization as a Precursor for Peptide Nucleic Acid (PNA) Monomers." Molecules 11, no. 6: 435-443.

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