Synthesis of the pentasaccharide repeating unit of lactosillan [correction of latosillan].
A pentasaccharide, beta-D-Man-(1-->2)-[beta-D-GlcNAc-(1-->4)]-alpha-L-Rha-(1-->4)-alpha-L-Rha-(1-->4)-alpha-L-Rha-1-OC8H17, representing the repeating unit of latosillan, was convergently synthesized from the building blocks, ethyl 2,3-O-isopropylidene-1-thio-alpha-l-rhamnopyranoside, 2-O-acetyl-3,4,6-tri-O-benzyl-beta-d-glucopyranosyl trichloroacetimidate, and 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-beta-d-glucopyranosyl trichloroacetimidate under standard glycosylation conditions. The target pentasaccharide showed acceptable differentiation-inducing activity on HL-60 cell lines at the dosages of 10-50 microg/mL.
Hua
Yuxia
Y
State Key Laboratory of Environmental Chemistry and Ecotoxicology, Research Center for Eco-Environmental Sciences, Chinese Academy of Sciences, Beijing 100085, China.
Xiao
Junjun
J
Huang
Yingshen
Y
Du
Yuguo
Y
D000818:Animals; D002454:Cell Differentiation / Q000187:drug effects; D045744:Cell Line, Tumor; D005947:Glucose / Q000031:analogs & derivatives / Q000737:chemistry; D018922:HL-60 Cells; D006801:Humans; D051379:Mice; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000494:pharmacology; D011134:Polysaccharides / Q000138:chemical synthesis / Q000494:pharmacology; D012210:Rhamnose / Q000031:analogs & derivatives / Q000737:chemistry
D009844:Oligosaccharides; D011134:Polysaccharides; C036281:lactosillan; D005947:Glucose; D012210:Rhamnose