| Pre-activation-based one-pot synthesis of an alpha-(2,3)-sialylated core-fucosylated complex type bi-antennary N-glycan dodecasaccharide. | |
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MedLine Citation:
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PMID: 18601234 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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Synthesis of N-glycans is of high current interests due to their important biological properties. A highly efficient convergent strategy based on the pre-activation method for assembly of the complex type core fucosylated bi-antennary N-glycan dodecasaccharide has been developed. Retrosynthetically, this extremely challenging target is broken down to three modules: a sialyl disaccharide, a glucosamine building block and a hexasaccharide diol acceptor. The sialyl disaccharide was easily obtained by selective activation of a new 5-N-trichloroacetyl protected sialyl donor in the presence of a thiogalactoside acceptor. The hexasaccharide diol module was produced by double mannosylation of a fucosylated tetrasaccharide acceptor, which in turn was generated by glycosylation of a alpha-fucosylated disaccharide with a beta-mannose containing disaccharide donor. The union of the three modules was performed in one-pot giving the fully protected dodecasaccharide in high yield. This synthesis is characterized by minimum protective group and aglycon adjustment on oligosaccharide intermediates, thus greatly enhancing the overall synthetic efficiency. The modular feature of this strategy suggests that this method can be readily adapted to the synthesis of a wide variety of N-glycan structures. |
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Authors:
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Bin Sun; Balasubramanian Srinivasan; Xuefei Huang |
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Publication Detail:
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Type: Journal Article; Research Support, N.I.H., Extramural; Research Support, U.S. Gov't, Non-P.H.S. |
Journal Detail:
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Title: Chemistry (Weinheim an der Bergstrasse, Germany) Volume: 14 ISSN: 0947-6539 ISO Abbreviation: Chemistry Publication Date: 2008 |
Date Detail:
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Created Date: 2008-08-06 Completed Date: 2008-10-07 Revised Date: 2011-03-25 |
Medline Journal Info:
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Nlm Unique ID: 9513783 Medline TA: Chemistry Country: Germany |
Other Details:
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Languages: eng Pagination: 7072-81 Citation Subset: IM |
Affiliation:
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Department of Chemistry, The University of Toledo, 2801 W. Bancroft Street, Toledo, OH 43606, USA. |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Carbohydrate Sequence Fucose / chemistry* Magnetic Resonance Spectroscopy Molecular Sequence Data Polysaccharides / chemical synthesis*, chemistry Sialic Acids / chemistry* |
| Grant Support | |
ID/Acronym/Agency:
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R01 GM 72667/GM/NIGMS NIH HHS; R01 GM072667-04/GM/NIGMS NIH HHS |
| Chemical | |
Reg. No./Substance:
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0/Polysaccharides; 0/Sialic Acids; 3713-31-3/Fucose |
| Comments/Corrections | |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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