Synthesis of 4'-O-acetyl-maltose and alpha-D-galactopyranosyl-(1-->4)-D-glucopyranose for biochemical studies of amylose biosynthesis.
The chemical synthesis of the title compounds as maltose analogs, in which the non-reducing end is modified by acetylation of the 4'-OH group or by reversing its configuration, is reported. For synthesis of the 4'-O-acetylated analog, beta-maltose was converted into its per-O-benzylated-4',6'-O-benzylidene derivative followed by removal of the benzylidene acetal function and selective silylation at C-6'. Acetylation at C-4' of the obtained silylated compound followed by removal of the benzyl ether protecting groups and subsequent desilylation afforded the desired analog. The other maltose analog was synthesized via the glycosidation reaction between the glycosyl donor, O-(2,3,4,6-tetra-O-benzyl-alpha/beta-D-galactopyranosyl)trichloroacetimidate and the glycosyl acceptor, phenyl 2,3,6-tri-O-benzyl-1-thio-beta-D-glucopyranoside followed by removal of the phenylthio group and debenzylation to provide the desired analog.
Motawia
M S
MS
Department of Plant Biology, The Royal Veterinary and Agricultural University, Copenhagen, Denmark. mosm@kvl.dk
Olsen
C E
CE
Denyer
K
K
Smith
A M
AM
Møller
B L
BL
D000688:Amylose / Q000096:biosynthesis* / Q000737:chemistry; D002236:Carbohydrate Conformation; D004187:Disaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008320:Maltose / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D013329:Structure-Activity Relationship
D004187:Disaccharides; D007202:Indicators and Reagents; C029794:acetylmaltose; C032103:4-O-alpha-D-galactopyranosyl-D-galactose; D008320:Maltose; D000688:Amylose