Glycoconjugate libraries

Lockhoff, O, An access to glycoconjugate libraries through multicomponent reactions, Angew. Chem. Int. Ed., 37, 3436-3439, 1998. 

M. J. Sofia. Generation of oligosaccharide and glycoconjugate libraries for drug discovery. DTT 1996,/, 27-34. 

The combinatorial construction of glycopeptide libraries dominates the work reported in the area of solid phase glycoconjugate library construction. In all of the reported glycopeptide libraries, preformed saccharides are appended to the peptide unit by amide bond construction via either a building blocks or convergent strategy [32-34]. Such approaches eliminate the need to construct a glycosidic bond on the solid phase however, they also limit the accessible diversity. 

The preparation of a C-glycoside glycoconjugate library was first described by Armstrong and co-woikers [59]. Applying the Ugi four component con-... 

Li J, Robertson DE, Short JM, Wang PG. Chemical and enzymatic synthesis of glycoconjugates. 5 one-pot regioselective synthesis of bioactive galactobiosides using a CLONEZYME thermophilic glycosidase library. Bioorg. Med. Chem. Lett. 1999 9 35-38. 

A library of glycoconjugate benzenesulfonamides that contain carbohydrate-triazole units has been evaluated for their ability to inhibit three human transmembrane carbonic anhy-drase isoz5mies hCA IX, hCA XII and hCA XIV which have potential as dmg targets OFig. 73 [118]. 

The stereoselective, one-step synthesis of (l,4)-5-thiodisaccharides (7-2) is a classical example (Scheme 2) of exploiting the excellent functionality of levoglucosenone as Michael reaction acceptor. The methodology of functionalization of C-2 either via conventional and stereoselective reduction, or oximation and then stereoselective reduction of the oximino functionality is unique in providing both classes of 5-thio-disaccharides. Moreover, the C-2 amino functionalized nonhydrolyzable 5-thio-disaccharide, after deprotection of C-2 acetamido function represents a convenient molecular scaffold for the generation of diverse libraries of peptidomimetics as a selected class of glycoconjugates. 

---