Thiodisaccharides with galactofuranose or arabinofuranose as terminal units: synthesis and inhibitory activity of an exo beta-D-galactofuranosidase.
Thiodisaccharides having beta-D-Galf or alpha-L-Araf units as non-reducing end have been synthesized by the SnCl(4)- or MoO(2)Cl(2)-promoted thioglycosylation of per-O-benzoyl-D-galactofuranose (1), its 1-O-acetyl analogue 4, or per-O-acetyl-alpha-L-arabinofuranose (16) with 6-thioglucose or 6-thiogalactose derivatives. After convenient removal of the protecting groups, the free thiodisaccharides having the basic structure beta-D-Galf(1-->6)-6-thio-alpha-D-Glcp-OMe (5) or beta-D-Galf(1-->6)-6-thio-alpha-D-Galp-OMe (15) were obtained. The respective alpha-L-Araf analogues 18 and 20 were prepared similarly from 16. Alternatively, beta-D-Galf(1-->4)-4-thio-3-deoxy-alpha-L-Xylp-OiPr was synthesized by Michael addition to a sugar enone of 1-thio-beta-d-Galf derivative, generated in situ from the glycosyl isothiourea derivative of 1. The free S-linked disaccharides were evaluated as inhibitors of the beta-galactofuranosidase from Penicillium fellutanum, being 15 and 20 the more active inhibitors against this enzyme.
Repetto
Evangelina
E
CIHIDECAR-CONICET, Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón 2, Ciudad Universitaria, 1428-Buenos Aires, Argentina.
Marino
Carla
C
Uhrig
M Laura
ML
Varela
Oscar
O
D001089:Arabinose / Q000031:analogs & derivatives* / Q000737:chemistry; D002384:Catalysis; D017606:Chlorine Compounds / Q000737:chemistry; D004187:Disaccharides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D005690:Galactose / Q000737:chemistry; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors* / Q000378:metabolism; D017895:Manganese Compounds / Q000737:chemistry; D010087:Oxides / Q000737:chemistry; D010407:Penicillium / Q000201:enzymology* / Q000378:metabolism; D013440:Sulfides / Q000737:chemistry; D017971:Tin Compounds / Q000737:chemistry
D017606:Chlorine Compounds; D004187:Disaccharides; D004791:Enzyme Inhibitors; D017895:Manganese Compounds; C522757:MoO2Cl2; D010087:Oxides; D013440:Sulfides; D017971:Tin Compounds; C431714:arabinofuranose; C041694:stannic chloride; D001089:Arabinose; D006026:Glycoside Hydrolases; C023112:exo-beta-D-galactofuranosidase; D005690:Galactose