Inframolecular studies of the protonation of adenophostin A: comparison with 1-D-myo-inositol 1,4,5-trisphosphate.
@article{Felemez1999InframolecularSO, title={Inframolecular studies of the protonation of adenophostin A: comparison with 1-D-myo-inositol 1,4,5-trisphosphate.}, author={M. Felemez and R. D. Marwood and B. Potter and B. Spiess}, journal={Biochemical and biophysical research communications}, year={1999}, volume={266 2}, pages={ 334-40 } }
Adenophostin A is a glyconucleotide natural product with the highest known potency for the D-myo-inositol 1,4,5-trisphosphate receptor. Using synthetic adenophostin A we have investigated the macroscopic and microscopic protonation process of this compound by performing (31)P NMR, (1)H NMR, and potentiometric titration experiments. The logarithms of the first to the fourth stepwise protonation constants are, respectively, log K(1) = 8.48, log K(2) = 6.20, log K(3) = 4.96, and log K(4) = 3.80… CONTINUE READING
Topics from this paper
15 Citations
Conformational and inframolecular studies of the protonation of adenophostin analogues lacking the adenine moiety.
- Chemistry, Medicine
- Biochimica et biophysica acta
- 2004
Structural determinants of adenophostin A activity at inositol trisphosphate receptors.
- Chemistry, Medicine
- Molecular pharmacology
- 2001
- 45
- PDF
Contribution of Phosphates and Adenine to the Potency of Adenophostins at the IP3 Receptor: Synthesis of All Possible Bisphosphates of Adenophostin A
- Chemistry, Medicine
- Journal of medicinal chemistry
- 2012
- 17
- PDF
Xylopyranoside-based agonists of D-myo-inositol 1,4,5-trisphosphate receptors: synthesis and effect of stereochemistry on biological activity.
- Chemistry, Medicine
- Carbohydrate research
- 2001
- 14
Inframolecular acid-base and coordination properties towards Na(+) and Mg(2+) of myo-inositol 1,3,4,5,6-pentakisphosphate: a structural approach to biologically relevant species.
- Chemistry, Medicine
- Dalton transactions
- 2013
- 8
- PDF
Inframolecular acid–base studies of the tris and tetrakis myo-inositol phosphates including the 1,2,3-trisphosphate motif
- Chemistry
- 2002
- 15
Adenophostins: High-Affinity Agonists of IP(3) Receptors.
- Chemistry, Medicine
- Current topics in membranes
- 2010
- 19
- Highly Influenced
References
SHOWING 1-10 OF 31 REFERENCES
Molecular recognition of adenophostin, a very potent Ca2+ inducer, at the D-myo-inositol 1,4,5-trisphosphate receptor.
- Chemistry, Medicine
- Biochemistry
- 1999
- 30
Influence of Mg2+ and pH on n.m.r. spectra and radioligand binding of inositol 1,4,5-trisphosphate.
- Chemistry, Medicine
- The Biochemical journal
- 1991
- 23
Self-association and protonation of adenosine 5'-monophosphate in comparison with its 2'- and 3'-analogues and tubercidin 5'-monophosphate (7-deaza-AMP).
- Chemistry, Medicine
- European journal of biochemistry
- 1987
- 117
Studies of inter- and intramolecular interaction in mononucleotides by proton magnetic resonance.
- Chemistry, Medicine
- Journal of the American Chemical Society
- 1968
- 255
- PDF
Nuclear magnetic resonance as a tool for determining protonation constants of natural polyprotic bases in solution.
- Chemistry, Medicine
- Analytical biochemistry
- 1995
- 325
A conformationally restricted cyclic phosphate analogue of inositol trisphosphate: synthesis and physicochemical properties
- Chemistry
- 1998
- 23
Synthesis, calcium mobilizing, and physicochemical properties of D-chiro-inositol 1,3,4,6-tetrakisphosphate, a novel and potent ligand at the D-myo-inositol 1,4,5-trisphosphate receptor.
- Chemistry, Medicine
- Journal of medicinal chemistry
- 1999
- 17
Adenophostins, newly discovered metabolites of Penicillium brevicompactum, act as potent agonists of the inositol 1,4,5-trisphosphate receptor.
- Biology, Medicine
- The Journal of biological chemistry
- 1994
- 177