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Org Biomol Chem ; 13(46): 11208-19, 2015 Dec 14.
Article in English | MEDLINE | ID: mdl-26381107

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.


Subject(s)
Anticoagulants/chemistry , Disaccharides/chemistry , Glucosamine/analogs & derivatives , Glycosaminoglycans/chemistry , Heparin, Low-Molecular-Weight/analogs & derivatives , Heparin/analogs & derivatives , Oligosaccharides/chemistry , Alkylation , Anticoagulants/chemical synthesis , Crystallography, X-Ray , Disaccharides/chemical synthesis , Glucosamine/chemical synthesis , Glycosaminoglycans/chemical synthesis , Heparin/chemical synthesis , Heparin, Low-Molecular-Weight/chemical synthesis , Models, Molecular , Oligosaccharides/chemical synthesis
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