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IP3 receptor-ligand. 2: Synthesis and molecular mechanics calculation of adenophostin A
H Hotoda1, M Takahashi, K Tanzawa
1Exploratory Chemistry Research Laboratories, Sankyo Co. Ltd, Tokyo, Japan.
Nucleic Acids Symposium Series
|January 1, 1995
Abstract:
The first total synthesis of adenophostin A, a potent IP3-receptor agonist, was accomplished by AgCIO4-gamma-collidine-promoted glycosylation employing 2-O-benzyl-3,4,6-tri-O-acetyl-alpha-D-glucopyranosyl bromide as a glycosyl donor. Stable conformations of both IP3 and adenophostin A were elucidated by molecular mechanics calculations. Three phosphorus atoms of the most stable conformations of IP3 and adenophostin A were superimposed by a rms deviation of 0.6 A, indicating that the phosphoryl groups adopt a similar spatial arrangement in both conformations.