502696-64-2Relevant academic research and scientific papers
Photoinduced electron transfer and chemical α-deoxygenation of D-galactono-1,4-lactone. Synthesis of 2-deoxy-D-lyxo-hexofuranosides
Chiocconi, Alejandro,Marino, Carla,Otal, Eugenio,De Lederkremer, Rosa M
, p. 2119 - 2126 (2007/10/03)
Two simple procedures for the synthesis of 2-deoxy-D-lyxo-hexono-1,4-lactone are described. Reductive cleavage of a 2-O-tosyl derivative of D-galactono-1,4-lactone in the presence of sodium iodide afforded the 2-deoxy derivative. On the other hand, α-deoxygenation of D-galactono-1,4-lactone was easily achieved by photochemical electron transfer deoxygenation of HO-2 as the 3-(trifluoromethyl)benzoate. Methyl 2-deoxy-β-D-lyxo-hexafuranoside ('methyl 2-deoxy-β-D-galactofuranoside') was synthesized and tested as substrate for exo β-D-galactofuranosidase from Penicillium fellutanum. The reaction was followed by HPAEC, showing that methyl 2-deoxy-β-D-galactofuranoside was not hydrolyzed by incubation with the enzyme. Neither the 2-deoxy lactone, nor the 2-deoxy-β-D-galactofuranoside acted as inhibitors of the reaction with the 4-nitrophenyl β-D-galactofuranoside. The present and our previous results show that the hydroxyl groups at C-2, C-3 and C-6 of the galactofuranoside are essential for interaction with the exo β-D-galactofuranosidase.
