Synthesis of c-linked glycosylated amino acids

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Project objective

Research objectives and content Glycopeptides play an important role in biology. For example, oxygen linked glycopeptides are believed to have a role in the resistance of the proteins to hydrolysis, and there has been some interest in the effects of glycosylation on the activity, stability and metabolism of glycosylated peptide drugs. The main synthetic (and operational) problem is that the glycosidic linkage is susceptible to both chemical and enzymatic cleavage, which limits the methods for the synthesis and the applicability of such compounds as drugs. To tackle the above mentioned problems a method for the synthesis of C-linked analogues of glycosylated amino acids (specifically of serine and threonine) will be developed and generalised. A number of selected key target compounds will be synthesised and characterised. The attention is drawn especially on the synthesis of difluoromethylene analogues, due to the well known superiority of the difluoromethylene group as an oxygen mimic. In addition, some new amino acid derived zinc reagents will be developed, characterised and applied for synthesis. Training content (objective, benefit and expected impact) The main benefit of this training is the collection of practical experience on a variety of different types of organic reactions. Furthermore, the project trains in asymmetric synthesis as well as in carbohydrate and peptide chemistry. Links with industry / industrial relevance (22) The project has industrial relevance, since it is concerned with the development of a general approach to the synthesis of analogues of glycopeptides which are of significant biological interest. The host research group has an on-going collaboration with Roche in this general area.

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Participants

• UNIVERSITY OF NEWCASTLE UPON TYNE · NEWCASTLE UPON TYNECoordinatorUnited Kingdom

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