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Published Online February 1, 2001
Science DOI: 10.1126/science.1057324

Reports

Submitted on November 9, 2000
Accepted on January 23, 2001

Automated Solid-Phase Synthesis of Oligosaccharides

Obadiah J. Plante 1, Emma R. Palmacci 1, Peter H. Seeberger 1*

1 Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA 02139, USA.

Traditionally, access to structurally defined complex carbohydrates has been very laborious. Although recent advancements in solid-phase synthesis have made the construction of complex oligosaccharides less tedious, a high level of technical expertise is still necessary to obtain the desired structures. We describe the first automated chemical synthesis of several oligosaccharides on a solid-phase synthesizer. A branched dodecasaccharide was synthesized through the use of glycosyl phosphate building blocks and a novel octenediol functionalized resin. The target oligosaccharide was readily obtained after cleavage from the solid support. Access to certain complex oligosaccharides now has become feasible in a fashion much like the construction of oligopeptides and oligonucleotides.


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Science. ISSN 0036-8075 (print), 1095-9203 (online)