Synthesis of a derivative of a-D-Glcp (1-2)-D-Galf suitable for further glycosylation and of a-D-Glcp (1-2)-D-Gal, a disaccharide fragment obtained from varianose.

MARINO, CARLA; LIMA, C; MARIÑO, K; MUCHNIK DE LEDERKREMER, R

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY

BEILSTEIN-INSTITUT

Lugar: Frankfurt; Año: 2012 vol. 8 p. 2142 - 2148

1860-5397

The presence of galactofuranoyl units in infectious microorganisms has prompted the study of the metabolic pathways involved in their incorporation in glycans. Penicillium varians is a non-pathogenic fungus that produces varianose, a polysaccharide containing both a- and b-D-Galf units, which can be used as a model for biosynthetic studies on a-d-Galf incorporation. Synthetic oligosaccharide fragments related to varianose are useful as potential substrates or standards for characterization of the a-galactofuranosyl transferases In this paper we report a straightforward procedure for the synthesis of a-d-Glcp(1 2)-d-Gal (1) and the use of this compound to monitor the natural disaccharide released from varianose by mild acid degradation. The synthesis, performed by the glycosylaldonolactone approach, involved a glucosylgalactofuranose derivative, suitable for the synthesis of higher oligosaccharides with an internal d-Galf.