Beilstein J. Org. Chem.2012,8, 2067–2071, doi:10.3762/bjoc.8.232
Abstract Safety-catch linkers are useful for solid-phase oligosaccharide synthesis as they are orthogonal to many common protective groups. A new acylsulfonamide safety-catchlinker was designed, synthesized and employed during glycosylations using an automated carbohydrate synthesizer. The analysis of the
cleavage products revealed shortcomings for oligosaccharide synthesis.
Keywords: glycosaminoglycans (GAGs); glycosylation; resins; safety-catchlinker; solid-phase synthesis; Findings
Solid-phase oligosaccharide synthesis [1][2] has been automated [3][4][5] to rapidly assemble complex oligosaccharides
product provides a terminal amine at the reducing end of the oligosaccharide for the fabrication of carbohydrate microarrays.
An acylsulfonamide safety-catchlinker 2 (Figure 1), was developed in combination with TentaGel resin to provide orthogonality to temporary ester protecting groups. This linker was
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Graphical Abstract
Figure 1:
Structures of two novel linkers on different resins.