Synthesis of Natural Products Utilizing Ring Cleavage Reaction of myo-Inositol Derivatives.

Synthesis of fluorodeoxy analogues of myo-inositol.

Accumulating evidence strongly suggests that the action of a phospholipase C on phosphoinositides in the cell membrane in response to the activation of a receptor is an integral part of an intracellular signalling pathway. Specific inhibitors of this enzyme and the site-specific kinases involved in inositide metabolism are urgently required to establish their function. An approach to the design...

Evidence for C-H cleavage by an iron-superoxide complex in the glycol cleavage reaction catalyzed by myo-inositol oxygenase.

myo-Inositol oxygenase (MIOX) activates O2 at a mixed-valent nonheme diiron(II/III) cluster to effect oxidation of its cyclohexan-(1,2,3,4,5,6-hexa)-ol substrate [myo-inositol (MI)] by four electrons to d-glucuronate. Abstraction of hydrogen from C1 by a formally (superoxo)diiron(III/III) intermediate was previously proposed. Use of deuterium-labeled substrate, 1,2,3,4,5,6-[2H]6-MI (D6-MI), has...

Stereochemistry of the myo-inositol-1-phosphate synthase reaction.

Experiments with D-glucose-6-P stereospecifically tritiated at C-6 showed that the myo-inositol-1 P synthase reaction catalyzed by both the enzyme from beef testis and from pollen of Lilium longiflorum proceeds with stereospecific loss of the pro-6R and incorporation of the pro-6S hydrogen into the product. The ring closure thus occurs in a retention mode at C-6 of the substrate, a finding at v...

Role of myo-inositol

Synthesis of natural products containing the pyrrolic ring.