INVESTIGADORES
UHRIG Maria Laura
artículos
Título:
Thiodisaccharides with galactofuranose or arabinofuranose as terminal units: Synthesis and inhibitory activity of an exo a-D-galactofuranosidase
Autor/es:
REPETTO, E.; MARINO, C.; UHRIG, M. L.; VARELA, O.
Revista:
BIOORGANIC & MEDICINAL CHEMISTRY.
Editorial:
Elsevier Science
Referencias:
Lugar: New York, USA; Año: 2009 p. 2703 - 2711
ISSN:
0968-0896
Resumen:
Thiodisaccharides having b-D-Galf or a-L-Araf units as non-reducing end have been synthesized by the SnCl4- or MoO2Cl2-promoted thioglycosylation of per-O-benzoyl-D-galactofuranose (1), its 1-O-acetyl analogue 4, or per-O-acetyl-a-L-arabinofuranose (16) with 6-thioglucose or 6-thiogalactose derivatives. After convenient removal of the protecting groups, the free thiodisaccharides having the basic structure b-D-Galf(1-6)-6-thio-a-D-Glcp-OMe (5) or b-D-Galf(1-5)-6-thio-a-D-Galp-OMe (15) were obtained. The respective a-L-Araf analogues 18 and 20 were prepared similarly from 16. Alternatively, b-D-Galf(1-4)-4-thio-3-deoxy-a-L-Xylp-OiPr was synthesized by Michael addition to a sugar enone of 1-thio-b-D-Galf derivative, generated in situ from the glycosyl isothiourea derivative of 1. The free S-linked disaccharides were evaluated as inhibitors of the b-galactofuranosidase from Penicillium fellutanum, being 15 and 20 the more active inhibitors against this enzyme