23567-96-6Relevant academic research and scientific papers
Variable-Temperature NMR Spectroscopy, Conformational Analysis, and Thermodynamic Parameters of Cyclic Adenosine 5′-Diphosphate Ribose Agonists and Antagonists
Saatori, Sarah-Marie,Perez, Tanner J.,Graham, Steven M.
, p. 2554 - 2569 (2018/03/09)
Cyclic adenosine 5′-diphosphate ribose (cADPR) is a ubiquitous Ca2+-releasing second messenger. Knowledge of its conformational landscape is an essential tool for unraveling the structure-activity relationship (SAR) in cADPR. Variable-temperature 1H NMR spectroscopy, in conjunction with PSEUROT and population analyses, allowed us to determine the conformations and thermodynamic parameters of the furanose rings, γ-bonds (C4′-C5′), and β-bonds (C5′-O5′) in the cADPR analogues 2′-deoxy-cADPR, 7-deaza-cADPR, and 8-bromo-cADPR. A significant finding was that, although the analogues are similar to each other and to cADPR itself in terms of overall conformation and population (ΔG°), there were subtle yet important differences in some of thermodynamic properties (ΔH°, ΔS°) associated with each of the conformational equilibria. These differences prompted us to propose a model for cADPR in which the interactions between the A2′-N3, A5″-N3, and H2-R5′ atoms serve to fine-tune the N-glycosidic torsion angles (χ).
A novel fluorescent probe for NAD-consuming enzymes
Pergolizzi, Giulia,Butt, Julea N.,Bowater, Richard P.,Wagner, Gerd K.
supporting information; experimental part, p. 12655 - 12657 (2012/01/12)
A novel, fluorescent NAD derivative is processed as substrate by three different NAD-consuming enzymes. The new probe has been used to monitor enzymatic activity in a continuous format by changes in fluorescence and, in one case, to directly visualize alt
Synthesis of cyclic adenosine 5′-diphosphate ribose analogues: A C2′ endo/syn "southern" ribose conformation underlies activity at the sea urchin cADPR receptor
Moreau, Christelle,Ashamu, Gloria A.,Bailey, Victoria C.,Galione, Antony,Guse, Andreas H.,Potter, Barry V. L.
experimental part, p. 278 - 290 (2011/02/23)
Novel 8-substituted base and sugar-modified analogues of the Ca 2+ mobilizing second messenger cyclic adenosine 5′-diphosphate ribose (cADPR) were synthesized using a chemoenzymatic approach and evaluated for activity in sea urchin egg homogenate (SUH) and in Jurkat T-lymphocytes; conformational analysis investigated by 1H NMR spectroscopy revealed that a C2′ endo/syn conformation of the "southern" ribose is crucial for agonist or antagonist activity at the SUH-, but not at the T cell-cADPR receptor.
A facile two-step synthesis of 8-arylated guanosine mono- and triphosphates (8-aryl GXPs)
Collier, Alice,Wagner, Gerd
, p. 4526 - 4532 (2008/09/19)
We report a simple and high-yielding two-step procedure for the preparation of 8-arylated guanosine mono- and triphosphates (8-aryl GXPs). The key step of our synthesis is the Suzuki-Miyaura coupling of unprotected 8-bromo GMP and 8-bromo GTP with various
