Saccharide solid-phase synthesis

Protocols of peptide chemistry and, to some extent, biooligomer synthesis (e.g., nucleotides, saccharides) are valuable sources of information on this topic with regards to solid-phase synthesis peculiarities. Here we focus on a particular functional group transformation, which takes the role of depro-tecting a masked functionality, namely the nitro-to-amine reduction. This approach provides a versatile tool for planning multistep derivatizations of heterocycles, as exemplified in Fig. 15.45... 

Frechet JMJ, Schuerch C. Solid-phase synthesis of oligosac- 87. charides III. Preparation of some derivatives of di- and tri-saccharides via a simple alcoholysis reaction. Carb Res. 1972 22 399-412. 

Glycomimetics Linked sugars Spaced sugars Functional mimetics Saccharide-peptide hybrids Sugar amino acids Solid phase synthesis Sialyl Lewis Carbohydrate medicinal chemistry... 

Synsorb. Because several of these supports are also used in solid-phase synthesis, an advantage of using carbohydrate-displaying beads as model systems for polyvalent recognition events is that libraries of saccharides can be assembled. Therefore, structure-function relationships can be determined rapidly. 

Hunt JA, Roush WR. Solid-phase synthesis of 6-deoxyoligo-saccharides. J. Am. Chem. Soc. 1996 118 9998 9999. 

Carbohydrates and polysaccharides, on the one hand, and peptides and proteins, on the other, have been considered as separate classes of natural products for a long time. Fundamental chemical methodology for the synthesis of both saccharides and peptides was developed by Emil Fischer et al. at the beginning of the 20th century. 1,2 However, the harsh conditions employed in early solution and solid-phase peptide synthesis hindered the combination of peptide and carbohydrate chemistry, i.e. glycopeptide synthesis. Considerable efforts were made to combine the two branches of natural product chemistry, and the state of the art within glycopeptide synthesis has improved dramatically during the last decades, as described in a number of reviews. 3 23,512"514 ... 

The improved availability of glycosyltransferases has led to increased use of che-moenzymatic synthesis, where chemical synthesis is combined with the use of glycosyltransferases to build up saccharides on a parent glycopeptide in solution or on solid phase (Section 6.3.3.6).1200"2061... 

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