By Peter H. Seeberger
ISBN-10: 0471378283
ISBN-13: 9780471378280
ISBN-10: 0471460729
ISBN-13: 9780471460725
Solid-phase synthesis of carbohydrates provides distinct demanding situations to artificial chemists and at present represents one of many preferred components of analysis in bioorganic chemistry. strong aid Oligosaccharide Synthesis and Combinatorial Carbohydrate Libraries addresses the interesting expectation that solid-phase meeting of oligosaccharides may have a primary effect at the box of glycobiology. This book information the methodologies presently investigated for the attachment of carbohydrates to beads, synthesis together with coupling ideas, and removing of the product from beads.With chapters written by way of eminent contributing authors, the cloth explores varied artificial thoughts, glycosylation protocols, using good helps as opposed to soluble polymeric helps, and "on-resin" analytical tools. great development within the box has set the degree for sturdy help Oligosaccharide Synthesis and Combinatorial Carbohydrate Libraries to supply a wealth of knowledge on such issues as:Specific oligosaccharide buildings utilized in sign transduction processesPreparation and screening of glycopeptide librariesSolid-phase carbohydrate synthesis
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Extra info for Solid Support Oligosaccharide Synthesis and Combinatorial Carbohydrate Libraries
Example text
Moreover, and perhaps most importantly for the broader context of glycoconjugate synthesis, the completed oligosaccharide construct would likely require retrieval from the solid matrix before conjugation to the peptide or lipid, unless this portion were already present as part of the linker to the solid support. In the other scenario, which we have found more novel, for reasons that will be explained shortly, the oligomer undergoing elongation is mounted to the solid support somewhere in the nonreducing region.
Reduction of the azide and coupling of the resulting anomerically pure (3-amino functionality would provide a protected glycopeptide. 45 Disaccharide 66 was extended in standard fashion to trisaccharide 67 and fully protected to give 68. This latter compound was treated with anthracenesulfonamide and I(5jm-coll)2ClO4 to form the intermediate 69. Reaction of the iodosulfonamide 69 with tetra-n-butylammonium azide followed by acetylation provided the anomeric azide 70. The anthracenesulfonamide linkage was cleaved under mild, solid support compatible conditions such as thiophenol or 1,3-propanedithiol and Hiinig's base.
A) Griffith, D. , and Danishefsky, S. , J. Am. Chem. Soc. , Nishida, A. , J. Am. Chem. Soc. 108,140-145 (1986). , Seeberger, P. , and Danishefsky, S. , Angew. , Int. Ed. 37, 786-789 (1998). , Roth, K. , Science 262, 1892-1895 (1993). 40 THE GLYCAL ASSEMBLY METHOD ON SOLID SUPPORTS 27. , Science 260, 159-160 (1993). 28. (a) Graham, D. , Lew, G. , Klein, P. , Evans, D. , Evans, D. , Saeed, Z. , and Malaty, H. , Awn. Int. Med. , Hirschl, A. , N. Engl. J. Med. 328, 308-312 (1993). 29. , in The Lectins: Properties, Functions and Applications in Biology and Medicine, Liener, I.
Solid Support Oligosaccharide Synthesis and Combinatorial Carbohydrate Libraries by Peter H. Seeberger
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