Abstract
We report a traceless photocleavable linker for the automated glycan assembly of carbohydrates with free reducing ends. The reductive-labile functionality in the linker tolerates all commonly used reagents and protocols for automated glycan assembly, as demonstrated with the successful preparation of nine plant cell wall-related oligosaccharides, and is cleaved by hydrogenolysis.
Highlights
We report a traceless photocleavable linker for the automated glycan assembly of carbohydrates with free reducing ends
We envisioned that the introduction of a benzyl moiety into photocleavable linker 1 would allow for rapid access to free reducing glycans after photo-induced cleavage of the glycans from the solid support followed by hydrogenolysis
We report the synthesis and use of traceless linker 2, whose applicability was demonstrated in the automated assembly of various complex glycans with free reducing ends (Fig. 1)
Summary
We report a traceless photocleavable linker for the automated glycan assembly of carbohydrates with free reducing ends. The reductive-labile functionality in the linker tolerates all commonly used reagents and protocols for automated glycan assembly, as demonstrated with the successful preparation of nine plant cell wall-related oligosaccharides, and is cleaved by hydrogenolysis. Starting from a resin-bound linker, iterative glycosylation and deprotection steps systematically elongate the glycan chain.
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