than myoinositol, stimulates cannabinoid synthesis.

T1 - The synthesis of homochiral inositol phosphates from myo-inositol

Thermal Cycling Cascade Biocatalysis of myo-Inositol Synthesis ..

N2 - myo-Inositol 3,4,5,6-tetrakisphosphate [Ins(3,4,5,6)P4] and its enantiomer exhibit distinct functions in the regulation of transepithelial chloride secretion. In search for agonists and antagonists of these potential messengers we synthesized a bicyclic oxepin analogue and a tricyclic analogue with a selfprotecting dioxolane moiety. The carbon backbone extension was linked to the C2 position. Ring closure was achieved by a metathesis reaction.

The novel and stereocontrolled synthesis of (±)-tetrodotoxin from myo-inositol is described

Synthesis of bi- and tricyclic analogues of myo-inositol …

N2 - A report of a new synthesis of nojirimycin (1a), as well as its antipode (1b), from optically active seven-membered hemiacetal lactones (2a,b) derived from myo-inositol by a five step reaction; the hydrogen sulphite adduct of (1b) shows high inhibitory activity against β-glucosidase and α-mannosidase, being almost comparable to that of mannojirimycin.

A report of a new synthesis of nojirimycin (1a), as well as its antipode (1b), from optically active seven-membered hemiacetal lactones (2a,b) derived from myo-inositol by a five step reaction; the hydrogen sulphite adduct of (1b) shows high inhibitory activity against β-glucosidase and α-mannosidase, being almost comparable to that of mannojirimycin.


Patent US5091549 - Synthesis of d-myoinositol-1 …

Ataxia telangiectasia (AT) is a complex autosomal recessive disorder that has been associated with a wide range of physiological defects including an increased sensitivity to ionizing radiation and abnormal checkpoints in the cell cycle. The mutated gene product, ATM, has a domain possessing homology to phosphatidylinositol-3-kinase and has been shown to possess protein kinase activity. In this study, we have investigated how AT affects myo-inositol metabolism and phospholipid synthesis using cultured human fibroblasts. In six fibroblast lines from patients with AT, myo-inositol accumulation over a 3-h period was decreased compared to normal fibroblasts. The uptake and incorporation of myo-inositol into phosphoinositides over a 24-h period, as well as the free myo-inositol content was also lower in some but not all of the AT fibroblast lines. A consistent finding was that the proportion of 32P in total labeled phospholipid that was incorporated into phosphatidylglycerol was greater in AT than normal fibroblasts, whereas the fraction of radioactivity in phosphatidic acid was decreased. Turnover studies revealed that AT cells exhibit a less active phospholipid metabolism as compared to normal cells. In summary, these studies demonstrate that two manifestations of the AT defect are alterations in myo-inositol metabolism and phospholipid synthesis. These abnormalities could have an effect on cellular signaling pathways and membrane production, as well as on the sensitivity of the cells to ionizing radiation and proliferative responses.

Synthesis of D-myoinositol-1-phosphate Abstract

AB - A new synthetic procedure for efficient conversion of myo-inositol into homochiral inositol phosphates is presented, and is illustrated with total synthesis of myo-inositol 1-phosphate, 2-deoxy-myo-inositol 1-phosphate, myo-inositol 3-phosphate, myo-inositol 4-phosphate, myo-inositol 1,4-bisphosphate, myo-inositol 1,4,5-trisphosphate, and myo-inositol 3,4,5,6-tetrakisphosphate. The syntheses start with selfresolving myo-inositol camphanylidene cis-monoacetals 2a and 2a′, which are obtained in one step from the parent cyclitol and D- and L-camphor dimethyl acetal, respectively, and are harvested conveniently by means of a precipitation driven equilibration. The syntheses feature in the key steps the selective monophosphorylation, selective bissilylation and selective trisacylation of 2a and 2a′, as well as the use of dibenzyl phosphorochloridate and 2-dimethylamino-5,6-benzo-1,3,2-dioxaphosphepane for effecting mono and polyphosphorylations, respectively. In support of stereochemical assignments an X-ray structure of one of the intermediate fully protected inositol derivatives is also presented.

Synthesis of the Enantiomers of 6-Deoxy-myo-Inositol …

N2 - A new synthetic procedure for efficient conversion of myo-inositol into homochiral inositol phosphates is presented, and is illustrated with total synthesis of myo-inositol 1-phosphate, 2-deoxy-myo-inositol 1-phosphate, myo-inositol 3-phosphate, myo-inositol 4-phosphate, myo-inositol 1,4-bisphosphate, myo-inositol 1,4,5-trisphosphate, and myo-inositol 3,4,5,6-tetrakisphosphate. The syntheses start with selfresolving myo-inositol camphanylidene cis-monoacetals 2a and 2a′, which are obtained in one step from the parent cyclitol and D- and L-camphor dimethyl acetal, respectively, and are harvested conveniently by means of a precipitation driven equilibration. The syntheses feature in the key steps the selective monophosphorylation, selective bissilylation and selective trisacylation of 2a and 2a′, as well as the use of dibenzyl phosphorochloridate and 2-dimethylamino-5,6-benzo-1,3,2-dioxaphosphepane for effecting mono and polyphosphorylations, respectively. In support of stereochemical assignments an X-ray structure of one of the intermediate fully protected inositol derivatives is also presented.