Abstract
d-Glucosamine derivatives bearing latent O4 functionality provide modified H/HS-type disaccharide donors for a final stage capping approach enabling introduction of conjugation-suitable, non-reducing terminal functionality to biologically important glycosaminoglycan oligosaccharides. Application to the synthesis of the first O4-terminus modified synthetic LMWH decasaccharide and an HS-like dodecasaccharide is reported.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Alkylation
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Anticoagulants / chemical synthesis
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Anticoagulants / chemistry*
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Crystallography, X-Ray
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Disaccharides / chemical synthesis
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Disaccharides / chemistry*
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Glucosamine / analogs & derivatives*
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Glucosamine / chemical synthesis
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Glycosaminoglycans / chemical synthesis
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Glycosaminoglycans / chemistry*
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Heparin / analogs & derivatives*
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Heparin / chemical synthesis
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Heparin, Low-Molecular-Weight / analogs & derivatives*
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Heparin, Low-Molecular-Weight / chemical synthesis
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Models, Molecular
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Oligosaccharides / chemical synthesis
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Oligosaccharides / chemistry*
Substances
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Anticoagulants
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Disaccharides
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Glycosaminoglycans
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Heparin, Low-Molecular-Weight
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Oligosaccharides
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Heparin
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Glucosamine