l-Iduronic acid derivatives as glycosyl donors

• Published in: Carbohydrate research Vol. 281; no. 2; pp. 253 - 276
• Main Authors: Tabeur, Christine, Machetto, Françoise, Mallet, Jean-Maurice, Duchaussoy, Philippe, Petitou, Maurice, Sinaÿ, Pierre
• Format: Journal Article
• Language: English
• Published: AMSTERDAM Elsevier Ltd 23.02.1996; Elsevier
• Subjects: Biochemistry & Molecular Biology; Carbohydrate Sequence; Chemistry; Chemistry, Applied; Chemistry, Organic; Fluorides - chemistry; Glycosaminoglycans; Glycosidation; Glycosyl donors; Glycosylation; Iduronic acid; Iduronic Acid - analogs & derivatives; Iduronic Acid - chemistry; Life Sciences & Biomedicine; Molecular Sequence Data; Physical Sciences; Science & Technology; Synthesis; Glycosyl donors; Glycosaminoglycans; Synthesis; Iduronic acid; Glycosidation; THIOGLYCOSIDES; glycosaminoglycans synthesis; HIGH-AFFINITY; HEPARIN FRAGMENTS; CHEMICAL SYNTHESIS; SALT; PENTASACCHARIDE; glycosyl donors; DERMATAN SULFATE; iduronic acid; ANTITHROMBIN-III; TRISACCHARIDE; BINDING SEQUENCE; glycosidation
• ISSN: 0008-6215; 1873-426X
• DOI: 10.1016/0008-6215(95)00346-0

O-[Methyl (2- O-acetyl-3- O-benzyl-4- O-levulinyl- α, and β l-idopyranosid)uronate] trichloroacetimidate and the corresponding n-pentenyl glycosides are efficient l-iduronic acid glycosyl donors. Both have been used for the high-yielding synthesis of basic disaccharide blocks which are useful for the subsequent synthesis of complex oligosaccharides related to heparin/heparan sulfate, and dermatan sulfate. In contrast, the corresponding thioethyl glycosides, thiophenyl glycosides, and fluoride, did not yield the expected disaccharides.