Carbohydrate-Based Scaffolds for the Generation of Sortiments of Bioactive Compounds

Summary.  The polyfunctionality and conformational rigidity of carbohydrates make this class of compounds ideal scaffolds for the production of sortiments¹ of bioactive compounds. Examples of carbohydrate-derived peptidomimetics of biological interest, such as somatostatin agonists and integrin antagonists, are presented. In order to have access to solid phase supported sortiments of compounds, orthogonally protected or unprotected carbohydrates were linked to polymers and reacted in the solid phase employing different regioselective strategies. Original bicyclic and tricyclic glycidic scaffolds were easily obtained starting from natural sugars such as D-arabinose and D-fructose. Manipulation of these conformationally blocked compounds afforded different carbohydrate-based derivatives, among which azidoacids are useful precursors of β-turn peptidomimetics. Received September 10, 2001. Accepted November 2, 2001