Synthesis of carbohydrate-centered oligosaccharide mimetics equipped with a functionalized tether.
Synthetic glycoclusters have gained substantial attention as mimetics of multivalent glycoconjugates. For their proposed glycobiological applications, it is advantageous to incorporate a functionalized tether into the clusters, which allows coupling to solid supports and other molecules such as reporter groups or even bioactive molecules. We herein report the use of carbohydrates as oligofunctional scaffolds for the synthesis of tethered cluster mannosides. Glycocluster 11 was prepared following two different pathways, starting either from glucose or the nonreducing disaccharide trehalose. The oligo alcohols 5 and 14 served as acceptors in the subsequent oligo-mannosylation reaction, in which three main problems were overcome: (i) incomplete glycosylation, (ii) cleavage of the core-glycoside, and (iii) ortho ester formation. Optimum conditions for the glycosylation were identified utilizing an advanced MALDI-TOF protocol.
Dubber
M
M
Institute of Organic Chemistry, Christian-Albrechts-University, Kiel, Germany.
Lindhorst
T K
TK
D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D009682:Magnetic Resonance Spectroscopy; D018716:Molecular Mimicry; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization; D014199:Trehalose / Q000737:chemistry
D009844:Oligosaccharides; D014199:Trehalose