IP3 receptor-ligand. 2: Synthesis and molecular mechanics calculation of adenophostin A.
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.
Hotoda
H
H
Exploratory Chemistry Research Laboratories, Sankyo Co. Ltd, Tokyo, Japan.
Takahashi
M
M
Tanzawa
K
K
Takahashi
S
S
Miyamoto
S
S
Kaneko
M
M
D000241:Adenosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism; D015220:Calcium Channels / Q000378:metabolism*; D015544:Inositol 1,4,5-Trisphosphate / Q000737:chemistry / Q000378:metabolism*; D053496:Inositol 1,4,5-Trisphosphate Receptors; D008024:Ligands; D008722:Methods; D008968:Molecular Conformation; D015394:Molecular Structure; D018160:Receptors, Cytoplasmic and Nuclear / Q000819:agonists* / Q000378:metabolism*; D013816:Thermodynamics
D015220:Calcium Channels; D053496:Inositol 1,4,5-Trisphosphate Receptors; D008024:Ligands; D018160:Receptors, Cytoplasmic and Nuclear; C085029:adenophostin A; D015544:Inositol 1,4,5-Trisphosphate; D000241:Adenosine