1269466-50-3Relevant academic research and scientific papers
Active Site Mapping of Xylan-Deconstructing Enzymes with Arabinoxylan Oligosaccharides Produced by Automated Glycan Assembly
Senf, Deborah,Ruprecht, Colin,de Kruijff, Goswinus H. M.,Simonetti, Sebastián O.,Schuhmacher, Frank,Seeberger, Peter H.,Pfrengle, Fabian
, p. 3197 - 3205 (2017)
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.
Automated synthesis of arabinoxylan-oligosaccharides enables characterization of antibodies that recognize plant cell wall glycans
Schmidt, Deborah,Schuhmacher, Frank,Geissner, Andreas,Seeberger, Peter H.,Pfrengle, Fabian
supporting information, p. 5709 - 5713 (2015/03/31)
Monoclonal antibodies that recognize plant cell wall glycans are used for high-resolution imaging, providing important information about the structure and function of cell wall polysaccharides. To characterize the binding epitopes of these powerful molecular probes a library of eleven plant arabinoxylan oligosaccharides was produced by automated solid-phase synthesis. Modular assembly of oligoarabinoxylans from few building blocks was enabled by adding (2-naphthyl)methyl (Nap) to the toolbox of orthogonal protecting groups for solid-phase synthesis. Conjugation-ready oligosaccharides were obtained and the binding specificities of xylan-directed antibodies were determined on microarrays. Automated synthesis meets plant research: Automated synthesis of plant oligosaccharides provides molecular tools for the characterization of important biological probes in plant research. The binding specificities of a collection of xylan-directed monoclonal antibodies have been determined by means of carbohydrate microarrays equipped with synthetic arabinoxylan fragments (see figure).
One-pot strategies for the synthesis of the tetrasaccharide linkage region of proteoglycans
Huang, Teng-Yi,Zulueta, Medel Manuel L.,Hung, Shang-Cheng
supporting information; experimental part, p. 1506 - 1509 (2011/04/27)
A linker-attached tetrasaccharide corresponding to the linkage region of proteoglycans was synthesized via one-pot procedures from the silylated monosaccharide derivatives. Regioselective one-pot protection protocols were applied in generating the requisite monosaccharide building blocks whereas stereoselective one-pot glycosylation approaches were utilized to assemble the tetrasaccharide skeleton.
