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Automated Synthesis of Oligosaccharides
Author(s) -
Palmacci Emma R.,
Plante Obadiah J.,
Hewitt Michael C.,
Seeberger Peter H.
Publication year - 2003
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200390331
Subject(s) - tetrasaccharide , chemistry , oligosaccharide , linker , elicitor , solid phase synthesis , yield (engineering) , stereochemistry , glycosylation , biochemistry , polysaccharide , peptide , materials science , computer science , metallurgy , operating system , gene
The chemical synthesis of oligosaccharides with an automated solid‐phase synthesizer is described. An octenediol linker served to attach the growing oligosaccharide chain to the solid support, and the desired structures were cleaved from the support via olefin metathesis to afford a pentenyl glycoside. The automated syntheses of several important carbohydrates, including a pentarhamnoside, a proteoglycan linkage‐region tetrasaccharide, a phytoalexin elicitor dodecasaccharide, and a branched Leishmania lipophosphoglycan tetrasaccharide, were accomplished in higher overall yield and ca. 20 times faster than with solution‐phase methods.