Neoglycoconjugates, Part B: Biomedical Applications by Y. C. Lee, Reiko T. Lee (Eds.)

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By Y. C. Lee, Reiko T. Lee (Eds.)

Neoglycoconjugates should not simply worthy for the fundamental figuring out of protein-carbohydrate interactions, yet they've got many sensible functions to boot. they're strong reagents in lots of telephone biology stories and ideal instruments for the isolation and characterization of animal and plant lectins, separation of cells, in addition to for the concentrating on of gear, man made vaccines, and diagnostic reagents. quantity 247 and its significant other quantity 242 comprise many useful tools on find out how to organize and use neoglycoconjugates. quantity 242 offers with synthesis and 247 with biomedical purposes

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G. Rice, P. Wu, L. Brand, and Y. C. Lee, Biochemistry 30, 6646 (1991). 34 OLIGOSACCHARIDE DERIVATIVES AND GLYCOPEPTIDES [2] glycopeptide. ~° The two conformers are spatially resolved because on folding the donor/acceptor distance changes from 20 to 10 A. An intriguing observation is the modulation of the ratio of the extended and folded conformation for each flexible antenna when changing the temperature between 0° and 40 °. ~ In this way, time-resolved fluorescence energy transfer provides data which can be used to estimate the value of thermodynamic constants for flexible glycosidic linkages in complex oligosaccharides.

6 g, 6 mmol) in acetonitrile (75 ml) is added aqueous tetrafluorohydroboric acid (48%, 2 ml). 2 ml) is added and the solvent evaporated in vacuo. The remaining oil is purified by flash chromatography in 2:1 (v/v) ethyl acetate/light petroleum ether. 44 (B). I0. 93. 1 Hz, 1H, H-I, Fuc). 99(C-1, Fuc). 2- A c etamido-4 ,6-di-O-ac etyl- 2-deoxy- 3-O-(2 ,3 ,4- tri- O-ac etyl-a- Lfucopyranosyl)-fl-o-glucopyranosylazide (10). 66 g, 3 mmol) in pyridine (50 ml) at 0 ° is added dropwise acetic acid anhydride (75 ml).

36 N-(9-Fluorenylmethoxycarbonyl)-4-O-benzyl-l-O-tert-butyl aspartate (18) is synthesized from 17 according to the general procedure for Fmoc amino acid esters given by Carpino and Han37: yield, 89%; mp 73°-74°; [a]~5 - 5 . 4 ° (c 1, CH3OH). N-9-Fluorenylmethoxycarbonylaspartic acid o~-tert-butyl ester (19) is synthesized from 18 by hydrogenolysis analogously to described procedures37'38; yield, 84%; amorphous; [a]~ - 1 5 . 5 ° (c 1, CH3OH). 5 ° (c 1, CH3OH). Synthesis of Disaccharide Asparagine Conjugates: General Procedure To a solution of the N-protected aspartic acid o~-tert-butyl ester 19 or 21 (12 mmol), in dichloromethane (50 ml) are added 5 ml (17 mmol) of IIDQ 29.

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