Synthesis of two heptasaccharide analogues of the lentinan repeating unit.
beta-D-Glcp-(1-->3)-beta-D-Glcp-(1-->3)-beta-D-Glcp-(1-->3)-beta-D-Glcp-(1-->3)-[beta-D-Glcp-(1-->3)-beta-D-Glcp-(1-->6)]-beta-D-Glcp (18) and the allyl glycoside of beta-D-Glcp-(1-->3)-[beta-D-Glcp-(1-->6)]-beta-D-Glcp-(1-->3)-beta-D-Glcp-(1-->3)-beta-D-Glcp-(1-->3)[-beta-D-Glcp-(1-->6)]-alpha-D-Glcp (29) were synthesized as the analogues of the lentinan repeating heptaose by building the pentasaccharide backbones first, followed by attaching the side chains. 4,6-O-benzylidenated mono-13 or disaccharide 8 were used as the acceptor to ensure the beta linkage in the synthesis of 18, while 4,6-O-benzylidenated disaccharides 21 and 23 were used as the donor and acceptor, respectively, to ensure the beta linkage in the synthesis of 29.
Zhao
Wei
W
Research Center for Eco-Environmental Sciences, Academia Sinica, PO Box 2871, Beijing 100085, PR China.
Yang
Guangbin
G
Kong
Fanzuo
F
D000276:Adjuvants, Immunologic / Q000138:chemical synthesis; D000970:Antineoplastic Agents / Q000138:chemical synthesis; D002236:Carbohydrate Conformation; D002855:Chromatography, Thin Layer; D005936:Glucans / Q000138:chemical synthesis / Q000737:chemistry; D005947:Glucose / Q000737:chemistry; D007912:Lentinan / Q000031:analogs & derivatives* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009844:Oligosaccharides / Q000138:chemical synthesis; D025942:Oligosaccharides, Branched-Chain / Q000138:chemical synthesis*; D009904:Optical Rotation; D021241:Spectrometry, Mass, Electrospray Ionization
D000276:Adjuvants, Immunologic; D000970:Antineoplastic Agents; D005936:Glucans; D009844:Oligosaccharides; D025942:Oligosaccharides, Branched-Chain; D007912:Lentinan; D005947:Glucose