596087-18-2Relevant articles and documents
Immobilization of UDP-Galactose on an Amphiphilic Resin
Bevan, Jessica G. M.,Louren?o, Eva C.,Chaves-Ferreira, Miguel,Rodrigues, Jo?o A.,Rita Ventura
supporting information, p. 908 - 914 (2018/02/27)
Nucleotide sugars are activated sugar precursors used by glycosyltransferases to form glycans. Here we report the first examples of resin-bound nucleotide sugars: fluorinated UDP-galactose and UDP-galactose. They were conjugated to a polyethylene glycol resin through the C6 position with an SMCC linker in good to excellent yields. This synthesis represents an efficient method to access resin-bound nucleotide sugars in a modular approach that enables modifications of the sugar or nucleotide before conjugation. The system has been conceived as a new chemistry-based screening system for enzymes that use UDP-galactose.
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 (2017/03/13)
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.
Total synthesis of anticoagulant pentasaccharide fondaparinux
Li, Tiehai,Ye, Hui,Cao, Xuefeng,Wang, Jiajia,Liu, Yonghui,Zhou, Lifei,Liu, Qiang,Wang, Wenjun,Shen, Jie,Zhao, Wei,Wang, Peng
, p. 1071 - 1080 (2014/05/20)
The anticoagulant pentasaccharide fondaparinux was synthesized using an improved and optimized synthetic strategy including a convergent [3+2] coupling approach, orthogonal protecting groups and various glycosyl donors. The new methods of glycosylation were also used for controlling the stereochemical configuration and improving the yield of the glycosylation. In addition, HPLC and NMR methods to monitor the process of total synthesis of fondaparinux were employed. This work provides a comprehensive elaboration for the synthesis and analysis of fondaparinux based on related literature, as well as abundant information for the synthesis of heparin-like oligosaccharides. A matter of protection! The anticoagulant pentasaccharide fondaparinux was synthesized using an improved and optimized synthetic strategy. The process of total synthesis was monitored by HPLC and NMR. This work will contribute to continued improvement of the multistep production of fondaparinux and provide abundant information for the synthesis of heparin-like oligosaccharides.
