Active Site Mapping of Xylan-Deconstructing Enzymes with Arabinoxylan Oligosaccharides Produced by Automated Glycan Assembly
| Autor: | Goswinus H. M. de Kruijff, Frank Schuhmacher, Fabian Pfrengle, Colin Ruprecht, Peter H. Seeberger, Sebastián Osvaldo Simonetti, Deborah Senf |
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| Jazyk: | angličtina |
| Rok vydání: | 2017 |
| Předmět: |
Glycan
Glycoside Hydrolases Stereochemistry Oligosaccharides SOLID-PHASE SYNTHESIS Xylose 010402 general chemistry ARABINOXYLAN PLANT CELL WALL 01 natural sciences Catalysis Substrate Specificity purl.org/becyt/ford/1 [https] chemistry.chemical_compound Hydrolysis Cellvibrio Glucuronoxylan Catalytic Domain Arabinoxylan purl.org/becyt/ford/1.4 [https] Organic chemistry Bacteroides Glycoside hydrolase Solid-Phase Synthesis Techniques chemistry.chemical_classification biology 010405 organic chemistry CARBOHYDRATES Otras Ciencias Químicas Organic Chemistry Ciencias Químicas Active site General Chemistry Xylan 0104 chemical sciences carbohydrates (lipids) Xylosidases chemistry biology.protein Xylans ENZYMES CIENCIAS NATURALES Y EXACTAS |
| Zdroj: | CONICET Digital (CONICET) Consejo Nacional de Investigaciones Científicas y Técnicas instacron:CONICET |
| DOI: | 10.1002/chem.201605902 |
| Popis: | Xylan-degrading enzymes are crucial for the deconstruction of hemicellulosic biomass, making the hydrolysis products available for various industrial applications such as the production of biofuel. 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. Fil: Senf, Deborah. Max Planck Institut für Kolloid und Grenzflächenforschung; Alemania. Freie Universität; Alemania Fil: Ruprecht, Colin. Max Planck Institut für Kolloid und Grenzflächenforschung; Alemania Fil: de Kruijff, Goswinus H. M.. Max Planck Institut für Kolloid und Grenzflächenforschung; Alemania. Freie Universität; Alemania. University Mainz. Institute of Institute of Organic Chemistry, Johannes Gutenberg; Alemania Fil: Simonetti, Sebastián Osvaldo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina. Max Planck Institut für Kolloid und Grenzflächenforschung; Alemania Fil: Schuhmacher, Frank. Max Planck Institut für Kolloid und Grenzflächenforschung; Alemania. Freie Universität; Alemania Fil: Seeberger, Peter H.. Max Planck Institut für Kolloid und Grenzflächenforschung; Alemania. Freie Universität; Alemania Fil: Pfrengle, Fabian. Max Planck Institut für Kolloid und Grenzflächenforschung; Alemania. Freie Universität; Alemania |
| Databáze: | OpenAIRE |
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