Enantiopure 1,2,3-Triazolyl-β-amino Acids via Click Cycloaddition Reaction on Racemic Alkynyl Precursors Followed by Separation of Stereoisomers

ISSN: 1873-5294 (Online)
ISSN: 1568-0266 (Print)


Volume 14, 24 Issues, 2014


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Current Topics in Medicinal Chemistry

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Enantiopure 1,2,3-Triazolyl-β-amino Acids via Click Cycloaddition Reaction on Racemic Alkynyl Precursors Followed by Separation of Stereoisomers

Author(s): Margarita Escudero-Casao, Alberto Vega-Penaloza and Eusebio Juaristi

Affiliation: Departamento de Quimica, Centro de Investigacion y de Estudios Avanzados del Instituto Politecnico Nacional, Apartado Postal 14-740, 07000 Mexico D. F., Mexico.

Abstract

In recent years, peptidomimetics have gained enormous importance in drug design aiming to achieve increased drug metabolic stability and higher selectivity. In the field of peptidomimetics, β-peptides incorporating β2- and β3-amino acids (the higher homologs of natural α-amino acids) provide a powerful method for the synthesis of peptidomimetics with particular secondary structures. In this regard, 1,2,3-triazole-modified peptidomimetics can act as effective peptide surrogates, and therefore have gained considerable attention. In the present report, 1,4-disubstituted 1,2,3-triazoles attached to β-amino acids were prepared selectively from the corresponding alkynyl-β2-amino acids according to Huisgen’s copper-catalyzed 1,3-dipolar cycloaddition (CuAAC), under mild conditions and with very high efficiency. Different azide derivatives, including some incorporating α-amino acids, were employed in this cycloaddition reaction. The enantiopure compounds were obtained via diastereomeric salt formation with chiral adjuvants, and subsequent separation.




Keywords: Triazol, click-reaction, β-amino acids, peptidomimetics, enantio- and diastereoseparation.

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Article Details

Volume: 14
Issue Number: 10
First Page: 1257
Last Page: 1270
Page Count: 14
DOI: 10.2174/1568026614666140423110420
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