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automated solid-phase synthesis of glycosaminoglycans. With
this novel linker, inherent but previously unknown limitations
of the safety-catch concept for solid-phase oligosaccharide syn-
thesis were discovered. The sulfamyl group can be attacked by
excess glycosylating agent to give the unexpected resin-bound
N-glycoside, which may block additional reaction sequences
and extension of the oligosaccharide [28]. In addition, sodium
methoxide can directly cleave the sulfamyl group, prohibiting
its use in conjunction with safety-catch linkers in general. While
safety-catch linkers offer many attractive features for the solid-
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Supporting Information
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We thank the Max Planck Society for very generous support,
and the European Research Council (ERC Advanced Grant
AUTOHEPARIN to PHS) is also gratefully acknowledged. We
thank Dr. V. Mountain for critically editing the manuscript.
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6. Guillier, F.; Orain, D.; Bradley, M. Chem. Rev. 2000, 100, 2091.
7. Plante, O. J.; Palmacci, E. R.; Seeberger, P. H. Science 2001, 291,
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9. Werz, D. B.; Castagner, B.; Seeberger, P. H. J. Am. Chem. Soc. 2007,
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10.Codée, J. D. C.; Kröck, L.; Castagner, B.; Seeberger, P. H.
11.Bindschädler, P. Different aspects of automeated heparin synthesis: de
novo synthesis of building blocks, a new linker, and synthesis of
heparin oligosaccharides. Ph.D. Thesis, Eidgenössische Technische
Hochschule Zürich, Switzerland, 2008.
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