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.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Animals
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Antiviral Agents / chemical synthesis
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Antiviral Agents / chemistry
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Antiviral Agents / pharmacology
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Chlorocebus aethiops
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Drug Design*
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Heparitin Sulfate / chemical synthesis*
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Heparitin Sulfate / chemistry
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Heparitin Sulfate / pharmacology*
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Herpesvirus 1, Human / drug effects*
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Host-Pathogen Interactions / drug effects*
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Humans
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Molecular Structure
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Oligosaccharides / chemical synthesis*
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Oligosaccharides / chemistry
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Oligosaccharides / pharmacology
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Receptors, Cell Surface / chemistry
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Sulfones / chemistry*
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Vero Cells
Substances
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Antiviral Agents
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Oligosaccharides
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Receptors, Cell Surface
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Sulfones
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Heparitin Sulfate
Associated data
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PubChem-Substance/123055462
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PubChem-Substance/123055463
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PubChem-Substance/123055464
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PubChem-Substance/123055465
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