INVESTIGADORES
VARELA Oscar Jose
congresos y reuniones científicas
Título:
Enantiospecific Synthesis of (2S, 5S)-5-Hydroxypipecolic Acid and a Tetrahydrofuran Sugar Amino Acid from D-Galactose
Autor/es:
UHRIG, MARIA LAURA; BALMACEDA, GUSTAVO; VARELA, OSCAR
Lugar:
Oslo, Noruega
Reunión:
Simposio; XXIV International Carbohydrate Symposium; 2008
Institución organizadora:
International Carbohydrate Organization
Resumen:
The amino acid 5-hydroxypipecolic acid (1) is a natural product that has been found in various plants (acacia, palm-dates) and microorganisms (i.e, Pseudomonas fluorescens). This amino acid has been described as a powerful inhibitor of platelet aggregation. We report here an enantioselective synthesis of 1 starting from D-galactose, via its 2-acetoxyglycal derivative 3. Additionally, one of the intermediates in the synthetic sequence was employed as precursor of the tetrahydrofuran amino acid 2. Pyranoid and furanoid sugar amino acids (SAA) are extensively used as conformational constrained scaffolds in peptidomimetic studies. Natural or synthetic cyclic amino acids incorporated into peptides confer rigidity, influencing cell recognition events.
