Document Detail


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