Synthesis of glucopyranoside-based ligands for D-myo-inositol 1,4,5-trisphosphate receptors.
@article{Riley2002SynthesisOG, title={Synthesis of glucopyranoside-based ligands for D-myo-inositol 1,4,5-trisphosphate receptors.}, author={A. Riley and D. Jenkins and R. D. Marwood and B. L. Potter}, journal={Carbohydrate research}, year={2002}, volume={337 12}, pages={ 1067-82 } }
Adenophostins A and B are naturally occurring glyconucleotides that interact potently with receptors for D-myo-inositol 1,4,5-trisphosphate, an important second messenger molecule in most cell types. Here we describe the design and synthesis of glucopyranoside-based analogues of adenophostin A lacking the adenine component. The key synthetic strategy involves glycosylation of selectively protected alcohols, derived from methyl beta-D-ribofuranoside or 1,4-anhydroerythritol, using glycosyl… CONTINUE READING
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References
SHOWING 1-10 OF 32 REFERENCES
2-Hydroxyethyl-alpha-D-glucopyranoside-2,3',4'-trisphosphate, a novel, metabolically resistant, adenophostin A and myo-inositol-1,4,5-trisphosphate analogue, potently interacts with the myo-inositol-1,4,5-trisphosphate receptor.
- Chemistry, Medicine
- Molecular pharmacology
- 1995
- 41
Contribution of the adenine base to the activity of adenophostin A investigated using a base replacement strategy.
- Chemistry, Medicine
- Journal of medicinal chemistry
- 2000
- 15
A Ca(2+)-mobilising carbohydrate-based polyphosphate: synthesis of 2-hydroxyethyl alpha-D-glucopyranoside 2',3,4-trisphosphate.
- Chemistry, Medicine
- Carbohydrate research
- 1996
- 28
Simplification of adenophostin A defines a minimal structure for potent glucopyranoside-based mimics of D-myo-inositol 1,4,5-trisphosphate.
- Chemistry, Medicine
- Bioorganic & medicinal chemistry letters
- 1999
- 16
Synthesis of selective non-Ca(2+)-mobilizing inhibitors of D-myo-inositol 1,4,5-trisphosphate 5-phosphatase.
- Chemistry, Medicine
- Journal of medicinal chemistry
- 1994
- 48
Identification of partial agonists with low intrinsic activity at the inositol-1,4,5-trisphosphate receptor.
- Chemistry, Medicine
- Molecular pharmacology
- 1993
- 25
Disaccharide polyphosphates based upon adenophostin A activate hepatic D-myo-inositol 1,4,5-trisphosphate receptors.
- Chemistry, Medicine
- Biochemistry
- 1997
- 43