SYNTHESIS OF CYCLIC D-alt-L PEPTIDOMIMETICS STARTING FROM A CARBOHYDRATE PRECURSOR

SOL C. PARAJÓN PUENZO; MARTIN LOPEZ VIDAL; SANDRA E. MARTÍN; OSCAR VARELA

DENVER

Congreso; ACS Summer School on Green Chemistry and Sustainable Energy; 2013

AMERICAN CHEMICAL SOCIETY

Fundamental building blocks used by nature are amalgamated to produce natural-like, yet unnatural, structural entities with multifunctional groups anchored in a single assembly. For example, hybrid molecules that maintain the basic structure of a carbohydrate have been obtained. These hybrid molecules include 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. 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. 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 was combined with D-alanine (R configuration) to give D-alt-L peptides to favor selfassembly processes.