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  Automated glycan assembly of oligo-N-acetyllactosamine and keratan sulfate probes to study virus-glycan interactions

Hahm, H. S., Bröcker, F., Kawasaki, F., Mietzsch, M., Heilbronn, R., Fukuda, M., et al. (2017). Automated glycan assembly of oligo-N-acetyllactosamine and keratan sulfate probes to study virus-glycan interactions. Chem, 2(1), 114-124. doi:10.1016/j.chempr.2016.12.004.

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Item Permalink: http://hdl.handle.net/11858/00-001M-0000-002C-3D86-F Version Permalink: http://hdl.handle.net/21.11116/0000-0006-595F-D
Genre: Journal Article

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Hahm, Heung Sik1, Author              
Bröcker, Felix2, Author              
Kawasaki, Fumiko, Author
Mietzsch, Mario, Author
Heilbronn, Regine, Author
Fukuda, Minoru, Author
Seeberger, Peter H.1, Author              
Affiliations:
1Peter H. Seeberger - Automated Systems, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society, ou_1863306              
2Chakkumal Anish, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society, ou_1863299              

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 Abstract: Oligo-N-acetyllactosamine (LacNAc) and keratan sulfate (KS) glycans exert crucial functions in disease-relevant processes, including cancer formation, inflammation, and viral infection. To facilitate structure-activity studies with these glycans, we established a universal strategy to synthesize linear and branched LacNAc as well as differentially sulfated KS oligosaccharides by automated glycan assembly. We synthesized oligosaccharides as long as hexamers by combining four monosaccharide building blocks. Key to the strategy was installing three orthogonal protection groups, 9-fluorenylmethoxycarbonyl (Fmoc), levulinoyl (Lev) ester, and 2-naphthylmethyl (Nap) ether, which were selectively removed from a common oligosaccharide precursor for differential sulfation. Microarrays presenting the synthetic oligosaccharides revealed a specific interaction between a disulfated KS tetrasaccharide and the adeno-associated virus AAVrh10 gene-therapy vector, which was further corroborated by surface plasmon resonance studies. Thus, KS represents a novel receptor candidate for AAVrh10. These insights could have implications for cell-type-specific gene-delivery approaches.

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 Dates: 2017-01-122017
 Publication Status: Published in print
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 Identifiers: DOI: 10.1016/j.chempr.2016.12.004
BibTex Citekey: Hahm2017114
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Title: Chem
Source Genre: Journal
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Publ. Info: Cambridge, MA : Cell Press
Pages: - Volume / Issue: 2 (1) Sequence Number: - Start / End Page: 114 - 124 Identifier: ISSN: 2451-9294