IP3 receptor-ligand. 2: Synthesis and molecular mechanics calculation of adenophostin a
Hotoda, H.; Takahashi, M.; Tanzawa, K.; Takahashi, S.; Miyamoto, S.; Kaneko, M.
Nucleic Acids Symposium Series 34: 163-164
1995
ISSN/ISBN: 0261-3166 PMID: 8841603 Document Number: 454315
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.