期刊
TETRAHEDRON
卷 66, 期 22, 页码 3951-3962出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2010.03.077
关键词
Synthesis; Uronic acid; Glucuronic acid; Iduronic acid; Glucosamine; Heparin; Heparan sulfate
资金
- Japan Science and Technology Agency [V07-05]
- Japan Ministry of Health, Labour and Welfare (MHLW)
- National Institutes of Health, USA [RO1 HL079182]
The monosaccharide moieties found in heparin (HP) and heparan sulfate (HS), glucosamine and two kinds of uronic acids, glucuronic and iduronic acids, were efficiently synthesized by use of glucosamine hydrochloride and glucurono-6,3-lactone as starting compounds. In the synthesis of the disaccharide building block, the key issues of preparation of uronic acids (glucuronic acid and iduronic acid moieties) were achieved in 12 steps and 15 steps, respectively, without cumbersome C-6 oxidation. The resulting monosaccharide moieties were utilized to the syntheses of HP/HS disaccharide building blocks possessing glucosamine-glucuronic acid (GlcN-GlcA) or iduronic acid (GlcN-IdoA) sequences. The disaccharide building blocks were also suitable for further modification such as glycosylation, selective deprotection, and sulfation. (C) 2010 Elsevier Ltd. All rights reserved.
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