The stepwise degradation of a glycosylated aldose. A potential method for sequencing branched oligosaccharides.
2,3,6,2',3',4',6'-Hepta-O-methylmaltose diethyl dithioacetal (2), obtained under mild conditions from N-methyl-hepta-O-methyl-N-p-nitrophenyl-beta-maltosylamine (1), was converted into the disulfone 4. Storage of a solution of 4 in aqueous tetrahydrofuran gave 1,2-dideoxy-1,1-bis(ethylsulfonyl)hepta-O-methylmalt-1-en itol (5). Fragmentation of 5 with aqueous ammonia released 2,3,4,6-tetra-O-methyl-D-glucose. The degradation procedure has potential for the sequencing of branched oligosaccharides.
Jäger
B
B
Institut für Organische Chemie und Biochemie, Universität Freiburg, Germany.
Lay
H
H
Lehmann
J
J
Ziser
L
L
D002240:Carbohydrate Sequence; D005634:Fructose-Bisphosphate Aldolase / Q000737:chemistry*; D006031:Glycosylation; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000737:chemistry*
D009844:Oligosaccharides; D005634:Fructose-Bisphosphate Aldolase