Abstract
The multigram-scale synthesis of a sulfation-site programmed heparin-like dodecasaccharide is described. Evaluation alongside dodecasaccharides lacking this single glucosamine O6-sulfation, or having per-O6-sulfation, shows that site-specific modification of the terminal glucosamine dramatically interconverts regulation of in vitro and in vivo biology mediated by the two important chemokines, CXCL12 (SDF1α) or CXCL8 (IL-8).
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Carbohydrate Sequence
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Cell Migration Assays, Leukocyte
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Chemokine CXCL12 / antagonists & inhibitors*
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Heparitin Sulfate / chemistry*
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Heparitin Sulfate / pharmacology*
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Human Umbilical Vein Endothelial Cells
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Humans
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Interleukin-8 / antagonists & inhibitors*
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Leukocytes
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Oligosaccharides / chemistry*
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Oligosaccharides / pharmacology*
Substances
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CXCL12 protein, human
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CXCL8 protein, human
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Chemokine CXCL12
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Interleukin-8
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Oligosaccharides
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Heparitin Sulfate