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  Active site mapping of xylan-deconstructing enzymes with arabinoxylan oligosaccharides produced by automated glycan assembly

Senf, D., Ruprecht, C., de Kruijff, G., Simonetti, S., Schuhmacher, F., Seeberger, P. H., et al. (2017). Active site mapping of xylan-deconstructing enzymes with arabinoxylan oligosaccharides produced by automated glycan assembly. Chemistry – A European Journal, 32(13), 3197-3205. doi:10.1002/chem.201605902.

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Item Permalink: http://hdl.handle.net/11858/00-001M-0000-002C-4C11-D Version Permalink: http://hdl.handle.net/21.11116/0000-0006-595A-2
Genre: Journal Article

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 Creators:
Senf, Deborah1, Author              
Ruprecht, Colin1, Author              
de Kruijff, Goswinus, Author
Simonetti, Sebastian, Author
Schuhmacher, Frank2, Author              
Seeberger, Peter H.2, Author              
Pfrengle, Fabian1, Author              
Affiliations:
1Fabian Pfrengle, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society, ou_1863303              
2Peter H. Seeberger - Automated Systems, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society, ou_1863306              

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Free keywords: carbohydrates solid-phase Synthesis plant cell wall arabinoxylan glycosyl hydrolases
 Abstract: Xylan-degrading enzymes are crucial for the deconstruction of hemicellulosic biomass, making the hydrolysis products available for various industrial applications such as biofuel production. To determine the substrate specificities of these enzymes, we prepared a collection of complex xylan oligosaccharides by automated glycan assembly. Seven differentially protected building blocks provided the basis for the modular assembly of 2-substituted, 3-substituted, and 2-/3-substituted arabino- and glucuronoxylan oligosaccharides. Elongation of the xylan backbone relied on iterative additions of C4-fluorenylmethoxylcarbonyl (Fmoc) protected xylose building blocks to a linker-functionalized resin. Arabinofuranose and glucuronic acid residues have been selectively attached to the backbone using fully orthogonal 2-(methyl)naphthyl (Nap) and 2-(azidomethyl)benzoyl (Azmb) protecting groups at the C2- and C3-hydroxyls of the xylose building blocks. The arabinoxylan oligosaccharides are excellent tools to map the active site of glycosyl hydrolases involved in xylan deconstruction. The substrate specificities of several xylanases and arabinofuranosidases were determined by analyzing the digestion products after incubation of the oligosaccharides with glycosyl hydrolases.

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 Dates: 2017-01-162017
 Publication Status: Published in print
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 Identifiers: DOI: 10.1002/chem.201605902
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Funding program : Emmy Noether program PF850/1-1 to FP and SFB 765
Funding organization : DFG

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Title: Chemistry – A European Journal
  Other : Chem. – Eur. J.
  Other : Chem. Eur. J.
Source Genre: Journal
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Publ. Info: Weinheim, Germany : VCH Verlagsgesellschaft
Pages: - Volume / Issue: 32 (13) Sequence Number: - Start / End Page: 3197 - 3205 Identifier: ISSN: 0947-6539