The synthesis of 2-, 3-, 4- and 6-O-alpha-D-glucopyranosyl-D-galactopyranose, and their evaluation as nutritional supplements for pre-term infants.
Four methods have been screened for the synthesis of some alpha-D-glucopyranosides, with the recently reported (Mukaiyama) combination of 2,3,4,6-tetra-O-benzyl-alpha-D-glucopyranosyl iodide and triphenylphosphine oxide being the most successful, especially in the diastereoselectivity exhibited. The alpha-D-glucopyranosides so obtained have been deprotected to yield 2-, 3-, 4- and 6-O-alpha-D-glucopyranosyl-D-galactopyranose. Only the last disaccharide showed any hydrolysis by alpha-glycosidases but this success was not emulated by mucosal extracts from the small intestine of the pig.
Meloncelli
Peter J
PJ
Chemistry M313, School of Biomedical, Biomolecular and Chemical Sciences, University of Western Australia, Crawley, WA 6009, Australia.
Williams
Tracey M
TM
Hartmann
Peter E
PE
Stick
Robert V
RV
D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D019587:Dietary Supplements; D004187:Disaccharides / Q000138:chemical synthesis* / Q000737:chemistry / Q000627:therapeutic use; D005690:Galactose / Q000627:therapeutic use*; D005960:Glucosides / Q000138:chemical synthesis* / Q000627:therapeutic use; D006801:Humans; D007225:Infant Food; D007231:Infant, Newborn; D007234:Infant, Premature; D008958:Models, Molecular
D004187:Disaccharides; D005960:Glucosides; D005690:Galactose