478529-37-2Relevant academic research and scientific papers
Chemical Synthesis of Residue-Selectively 13C and 2H Double-Isotope-Labeled Oligosaccharides as Chemical Probes for the NMR-Based Conformational Analysis of Oligosaccharides
Hamagami, Hiroki,Yamaguchi, Yoshiki,Tanaka, Hiroshi
, p. 16115 - 16127 (2020)
The conformational analysis of oligosaccharide is a fundamental issue in glycobiology. NMR measurements of atom-selectively 13C-labeled oligosaccharides have provided valuable information concerning their conformation, which would not be possible using nonlabeled oligosaccharides. The amount of accessible information from an atom-selectively labeled molecule, however, is limited. In this work, we report on the chemical synthesis of residue-selectively 13C- and 2H-labeled oligosaccharides and their use in conformational analysis. 1H NMR measurements of such double isotope-labeled compounds can provide a great deal of information on the dihedral angles across glycosidic linkages. We demonstrated this method in the conformational analyses of some linear and branched β(1,3)-glucan oligosaccharides.
Structure of the Complex between a Heparan Sulfate Octasaccharide and Mycobacterial Heparin-Binding Hemagglutinin
Huang, Teng-Yi,Irene, Deli,Zulueta, Medel Manuel L.,Tai, Tzu-Jui,Lain, Shih-Han,Cheng, Cheng-Po,Tsai, Ping-Xi,Lin, Shu-Yi,Chen, Zhi-Geng,Ku, Chiao-Chu,Hsiao, Chwan-Deng,Chyan, Chia-Lin,Hung, Shang-Cheng
supporting information, p. 4192 - 4196 (2017/04/04)
Heparin-binding hemagglutinin (HBHA) is a 199 amino acid virulence factor at the envelope of Mycobacterium tuberculosis that contributes to latent tuberculosis. The binding of HBHA to respiratory epithelial cells, which leads to extrapulmonary dissemination of the pathogen, is mediated by cell-surface heparan sulfate (HS). We report the structural characterization of the HBHA/HS complex by NMR spectroscopy. To develop a model for the molecular recognition, the first chemically synthesized uniformly 13C- and 15N-labeled HS octasaccharide and a uniformly 13C- and 15N-labeled form of HBHA were prepared. Residues 180–195 at the C-terminal region of HBHA show large chemical shift perturbation upon association with the octasaccharide. Molecular dynamics simulations conforming to the multidimensional NMR data revealed key electrostatic and even hydrophobic interactions between the binding partners that may aid in the development of agents targeting the binding event.
Solid-phase synthesis and 1H and 13C high-resolution magic angle spinning NMR of 13C-labeled resin-bound saccharides
Loening, Nikolaus M.,Kanemitsu, Takuya,Seeberger, Peter H.,Griffin, Robert G.
, p. 453 - 458 (2007/10/03)
We show how high-resolution magic angle-spinning NMR spectroscopy can be used to characterize 13C-labeled saccharides that have been prepared using solid-phase synthesis techniques while they are still bound to a solid-support resin. With the u
