Title: Synthesis of 3-O-sulfonated heparan sulfate octasaccharides that inhibit the herpes simplex virus type 1 host-cell interaction
Authors: Hu, Yu-Peng
Lin, Shu-Yi
Huang, Cheng-Yen
Zulueta, Medel Manuel L.
Liu, Jing-Yuan
Chang, Wen
Hung, Shang-Cheng
Department of Applied Chemistry
Issue Date: 1-Jul-2011
Abstract: Cell surface carbohydrates play significant roles in a number of biologically important processes. Heparan sulfate, for instance, is a ubiquitously distributed polysulfated polysaccharide that is involved, among other things, in the initial step of herpes simplex virus type 1 (HSV-1) infection. The virus interacts with cell-surface heparan sulfate to facilitate host-cell attachment and entry. 3-O-Sulfonated heparan sulfate has been found to function as an HSV-1 entry receptor. Achieving a complete understanding of these interactions requires the chemical synthesis of such oligosaccharides, but this remains challenging. Here, we present a convenient approach for the synthesis of two irregular 3-O-sulfonated heparan sulfate octasaccharides, making use of a key disaccharide intermediate to acquire different building blocks for the oligosaccharide chain assembly. Despite substantial structural differences, the prepared 3-O-sulfonated sugars blocked viral infection in a dosage-dependent manner with remarkable similarity to one another.
URI: http://dx.doi.org/10.1038/nchem.1073
ISSN: 1755-4330
DOI: 10.1038/nchem.1073
Volume: 3
Issue: 7
Begin Page: 557
End Page: 563
Appears in Collections:Articles