Synthesis of linear D-al-L peptidomimetics starting from a carbohydrate precursor

SOL C. PARAJÓN PUENZO; ADRIANA A. KOLENDER; SANDRA E. MARTÍN; OSCAR VARELA

Brasilia

Congreso; 14th Brazilian Meeting on Organic Synthesis; 2011

Brazilian Meeting on Organic Synthesis

INTRODUCTION Fundamental building blocks used by nature are amalgamated to produce natural-like, yet unnatural, structural entities with multifunctional groups anchored in a single ensemble. For example, hybrid molecules have been obtained that maintain the basic structure of a carbohydrate but have incorporated amino and carboxyl functional groups characteristic of amino acids. Diverse arrays of peptidic templates have been employed for the construction of homo- and heterooligomers that behave as peptidomimetics. These molecules are sometimes able to associate themselves spontaneously (self-assembly process) to form complex architectures.1 The novel materials find useful applications as microelectronics, drug delivery and tissue engineering. The linear oligopeptides are also precursor of cyclic peptoids (carbopeptoids) useful as molecular receptors.2 We describe herein the synthesis of an amino acid building block starting from inexpensive D-Glucono-1,5-lactone. As the amino containing stereocenter possesses the S configuration, the molecule is combined with D-alanine (R configuration) to give D-alt-L peptides to favor self-assembly processes.