913547-85-0Relevant academic research and scientific papers
Efficient Synthesis of a High-Mannose-Type Pentasaccharide and Hexasaccharide Related to N-Glycans
Jiang, Rui,Liang, Xiao-Mei,Jin, Shu-Hui,Lu, Hui-Zhe,Dong, Yan-Hong,Wang, Dao-Quan,Zhang, Jian-Jun
, p. 213 - 222 (2016)
Two high-mannose-type N-glycans, Man5 and Man6 oligosaccharides, were concisely synthesized from 4-methoxyphenyl α-d-mannopyranoside via 9 and 12 steps, and in 23% and 15% overall yields, respectively. The efficiency of the synthesis relies on the large-s
KinITC—One Method Supports both Thermodynamic and Kinetic SARs as Exemplified on FimH Antagonists
Zihlmann, Pascal,Silbermann, Marleen,Sharpe, Timothy,Jiang, Xiaohua,Mühlethaler, Tobias,Jakob, Roman P.,Rabbani, Said,Sager, Christoph P.,Frei, Priska,Pang, Lijuan,Maier, Timm,Ernst, Beat
supporting information, p. 13049 - 13057 (2018/08/17)
Affinity data, such as dissociation constants (KD) or inhibitory concentrations (IC50), are widely used in drug discovery. However, these parameters describe an equilibrium state, which is often not established in vivo due to pharmacokinetic effects and they are therefore not necessarily sufficient for evaluating drug efficacy. More accurate indicators for pharmacological activity are the kinetics of binding processes, as they shed light on the rate of formation of protein–ligand complexes and their half-life. Nonetheless, although highly desirable for medicinal chemistry programs, studies on structure–kinetic relationships (SKR) are still rare. With the recently introduced analytical tool kinITC this situation may change, since not only thermodynamic but also kinetic information of the binding process can be deduced from isothermal titration calorimetry (ITC) experiments. Using kinITC, ITC data of 29 mannosides binding to the bacterial adhesin FimH were re-analyzed to make their binding kinetics accessible. To validate these kinetic data, surface plasmon resonance (SPR) experiments were conducted. The kinetic analysis by kinITC revealed that the nanomolar affinities of the FimH antagonists arise from both (i) an optimized interaction between protein and ligand in the bound state (reduced off-rate constant koff) and (ii) a stabilization of the transition state or a destabilization of the unbound state (increased on-rate constant kon). Based on congeneric ligand modifications and structural input from co-crystal structures, a strong relationship between the formed hydrogen-bond network and koff could be concluded, whereas electrostatic interactions and conformational restrictions upon binding were found to have mainly an impact on kon.
36 branchings honeydews five sugar six sugar-to methoxyphenyl glycoside and its preparation method and application
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Paragraph 0108; 0110-0112, (2017/09/19)
The invention provides a 3,6-branched mannopentaose and hexaose on methoxy phenyl glycoside and a preparation method and an application thereof. A structural formula is shown in a formula I or a formula II; a compound can be used for preparing anti-HIV me
Facile synthesis of the pentasaccharide repeating unit of the exopolysaccharide from Cryptococcus neoformans serotype D
Zhuo, Xiao-Bin,Zou, Yan,Huang, Sheng-Jun,Liao, Jun,Hu, Hong-Gang,Zhao, Qing-Jie,Wu, Qiu-Ye
, p. 618 - 626 (2015/06/02)
Abstract β-D-GlcpA-(1→2)-[β-D-Xylp-(1→2)-α-D-Manp-(1→3)]-α-D-Manp-(1→3)-α-D-Manp, the repeating unit of the exopolysaccharide from Cryptococcus neoformans serotype D, was synthesized as its 4-methoxyphenyl glycoside. The approach presented here also provi
Synthesis of the 'primer-adaptor' trisaccharide moiety of Escherichia coli O8, O9, and O9a lipopolysaccharide
Liu, Chunjuan,Skogman, Fredrik,Cai, Ye,Lowary, Todd L.
, p. 2818 - 2825 (2008/04/06)
Described is the synthesis of the trisaccharide α-d-Manp-(1→3)-α-d-Manp-(1→3)-β-d-GlcpNAcO(CH 2)8N3, the glycan portion of which corresponds to the 'adaptor-primer' moiety linking the O-chain and core oligosaccharide in th
Sulfuric acid immobilized on silica: an efficient reusable catalyst for selective hydrolysis of the terminal O-isopropylidene group of sugar derivatives
Rajput, Vishal Kumar,Roy, Bimalendu,Mukhopadhyay, Balaram
, p. 6987 - 6991 (2007/10/03)
Sulfuric acid immobilized on silica proved to be an efficient catalyst for selective hydrolysis of the terminal O-isopropylidene group of sugar derivatives. The method is very simple and economic for large-scale synthesis in which the catalyst is recovered and reused for several runs. Reactions with di-O-isopropylidene derivatives of d-glucose, d-mannose, d-fructose and l-sorbose led to the formation of the corresponding mono-O-isopropylidene derivatives in good to excellent yields.
