GLYCAT · Glycosylation Catalysts

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Project objective

Catalysts for stereoselective glycosylations will be developed. The focus being on designing organocatalysts for catalyst-controlled glycosylations.Carbohydrates, the most abundant biomolecules on Earth, are intimately involved in manycrucial biological processes (signal transduction, cell recognition) and in diseases (AIDS,cancer). They are useful for the investigation of diseases, and have great potential as vaccinesand therapeutics. The biology depends on the specific identity (including stereochemistry) ofthe carbohydrates (usually oligosaccharides – several monosaccharides joined together).A significant bottleneck in making scientific progress in the strategically importantfield of glycoscience is the effort and expense required to synthesise pure oligosaccharidesand glycoconjugates as single stereochemical isomers. A major synthetic difficulty witholigosaccharides (vs. oligonucleotides or oligopeptides) is the diversity that can exist: a roughcalculation suggests that there are ~256 DNA tetranucleotides, ~160,000 tetrapeptides and>4x10^7 linear tetrasaccharides. Added permutations arise from the variety of monosaccharidestereoisomers and the different connectivities possible at each linkage. Many oligosacchardies are not linear but branched - adding further permutations.Given the impact of the ability to easily synthesise oligopeptides and oligonucleotides have had on modern biology, it is difficult to predict the impact of technology that would allow oligosaccharides to be synthesised with similar ease, other than that it would be highly significant. The proposal seeks to work towards this goal in a way that is complementary to approaches currently being used. Over the past 30 years stereoselective catalysis has transformed the availability of chiral molecules in enantiopure form. However, it has yet to make a similar impact on carbohydrate chemistry. GlyCat will be at the forefront of efforts to change the status quo in saccharide synthesis.

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Participants

• UNIVERSITY COLLEGE DUBLIN, NATIONAL UNIVERSITY OF IRELAND, DUBLIN · DublinCoordinatorIreland

Links

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