Saccharide Display on Microtiter Plates

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Presentation transcript:

Saccharide Display on Microtiter Plates Marian C Bryan, Oliver Plettenburg, Pamela Sears, David Rabuka, Shirley Wacowich-Sgarbi, Chi-Huey Wong Chemistry & Biology Volume 9, Issue 6, Pages 713-720 (June 2002) DOI: 10.1016/S1074-5521(02)00155-2

Figure 1 Olefin Metathesis with Subsequent Differentiation Stereocontrol was maintained in both the dihydroxylation and epoxidation steps. The remaining library member synthesis relied on rudimentary glycosidic coupling with BF3·OEt2 [17]. Rα = -(CH2)nCH3 (n = 5, 7, 9, 11, 13, 15, 17) and -(CH2)2C6H5. Rβ = -(CH2)nCH3 (n = 11, 13). R1 = -(CH2)nCH3 (n = 9, 15). R2 = -CO(CH2)13CH3 and -COCH2C6H5. R3 = -(CH2)nCH3 (n = 11, 12, 15) and -(CH2)6C6H5. Chemistry & Biology 2002 9, 713-720DOI: (10.1016/S1074-5521(02)00155-2)

Figure 2 Sulfuric Acid-Phenol Assay and Galactose Oxidase-Peroxidase Assay Figure 2A illustrates phenol in the presence of strong acid, generating the phenol adduct of the galactosyl lipid; this adduct is observable at 490 nm. Figure 2B shows the galactosyl lipid's oxidation by galactose oxidase as well as the indicator oxidized by the peroxidase. Both assays were performed in a microtiter plate. Chemistry & Biology 2002 9, 713-720DOI: (10.1016/S1074-5521(02)00155-2)

Figure 3 Ricin B Chain Binding The alkaline phosphatase conjugated to the goat anti-rabbit immunoglobin converts p-nitrophenyl phosphate to p-nitrophenol, which is observable at 405 nm. Chemistry & Biology 2002 9, 713-720DOI: (10.1016/S1074-5521(02)00155-2)

Figure 4 Selected Oligosaccharides R = -(CH2)13CH3 and R1 = -(CH2)5NHCO(CH2)11CH3. Chemistry & Biology 2002 9, 713-720DOI: (10.1016/S1074-5521(02)00155-2)

Figure 5 Oligosaccharide-Lectin Binding Assays Oligosaccharides 32, 34, and 35 were analyzed with ConA for α-glucose, whereas 36 and 37 were evaluated with TP for α-fucose. Both lectins were conjugated with a peroxidase, and lectin binding was observed by ABTS oxidation at 405 nm. Chemistry & Biology 2002 9, 713-720DOI: (10.1016/S1074-5521(02)00155-2)