| Towards the assembly of heparin and heparan sulfate oligosaccharide libraries: efficient synthesis of uronic acid and disaccharide building blocks. | |
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MedLine Citation:
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PMID: 20473366 Owner: NLM Status: Publisher |
Abstract/OtherAbstract:
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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. |
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Authors:
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Akihiro Saito; Masahiro Wakao; Hiroshi Deguchi; Aya Mawatari; Michael Sobel; Yasuo Suda |
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Publication Detail:
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Type: JOURNAL ARTICLE |
Journal Detail:
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Title: Tetrahedron Volume: 66 ISSN: 0040-4020 ISO Abbreviation: - Publication Date: 2010 May |
Date Detail:
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Created Date: 2010-7-13 Completed Date: - Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 2984170R Medline TA: Tetrahedron Country: - |
Other Details:
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Languages: ENG Pagination: 3951-3962 Citation Subset: - |
Affiliation:
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Department of Chemistry, Biotechnology, and Chemical Engineering, Graduate School of Science and Engineering, Kagoshima University, 1-21-40 Kohrimoto, Kagoshima 890-0065, Japan. |
Export Citation:
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Descriptor/Qualifier:
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| Grant Support | |
ID/Acronym/Agency:
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R01 HL079182-01A1//NHLBI NIH HHS; R01 HL079182-02//NHLBI NIH HHS; R01 HL079182-03//NHLBI NIH HHS; R01 HL079182-04//NHLBI NIH HHS |
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