Myoinositol, 133

Ethers of benzenepentol have been obtained by Dakin oxidation of the appropriately substituted acetophenone. Thus, the oxidation of 2-hydroxy-3,4,6-ttimethoxyacetophenone and 2-hydroxy-3,4,5-ttimethoxyacetophenone with hydrogen peroxide ia the presence of alkali gives l,2-dihydroxy-3,4,6-ttimethoxybenzene and l,2-dihydroxy-3,4,5-ttimethoxybenzene, respectively further methylation of these ethers yields the pentamethyl ether of benzenepentol (mp 58—59 degC) (253). The one-step aromatization of myoinositol to produce esters of pentahydroxybenzene is achieved by treatment with carboxylic acid anhydrides ia DMSO and ia the presence of pyridine (254) (see Vitamins). 6-Alkyl- or... 

Inositols, ie, hexaliydrobenzenehexols, are sugars that have received increasing study and are useful in the treatment of a wide variety of human disorders, including vascular disease, cancer, cirrhosis of the Hver, frostbite, and muscular dystrophy (269). Myoinositol esters prepared by reaction with lower fatty acid anhydrides are useful as Hver medicines and nonionic surfactants the aluminum and ammonium salts of inositol hexasulfate are useful anticancer agents (270). Tetraarjloxybenzoquinones are intermediates in the preparation of dioxazine dyes (266,271). The synthesis of hexakis(aryloxy)benzenes has also beenpubUshed (272). 

Myoinositol bis(trichloroethyl)phosphates were not as stable to pyridine at 20°, as were the related benzyl analogs. ... 

On the basis of experiments with myoinositol (50), it has been suggested that triose reductone should be oxidized by periodate to yield two molar equivalents of formic acid and one molar equivalent of carbon dioxide. However, it has been reported by two groups (1,29) that crystalline triose reductone is oxidized by two moles of periodic acid to give formic acid and glyoxylic acid, free iodine being liberated during the... 

The first three carba-sugars were synthesized by McCasIand and coworkers. Two other carba-sugars were prepared from myoinositol, and the remaining eleven carba-sugars have been synthesized from the Diels-Alder adduct of furan and acrylic acid. Conformational assignments of the carba-sugars were established with the aid of H-n.m.r. spectroscopy. 

The inositol is present in ph osphatidylinositol as the stereoisomer, myoinositol (Figure 14—8). Phosphatidylinositol 4,5-hisphosphate is an important constituent of cell membrane phosphohpids upon stimulation by a suitable hormone agonist, it is cleaved into diacylglycerol and inositol trisphosphate, both of which act as internal signals or second messengers. 

A. Inositol Phosphates.—Phosphatidyl inositol (71) is hydrolysed in mammalian tissues to wyo-inositol 1,2-cyclic phosphate (72).i myoinositol 1-phosphate (73) is released simultaneously but is not converted into (72) by the enzyme system. Periodate oxidation of (73) liberates orthophosphate quantitatively, the unstable dialdehyde phosphate (74) being an intermediate. Little or no orthophosphate is released from glucose 6-phosphate under the same oxidative conditions, and this reaction has been used to assay (73). 

McClure, C.K., Hansen, K.B., Herzog, K.J., Link, J.S., and Arnold, F.P., Diels-Alder reactivity of a keto vinylphosphonate. Empirical and theoretical observations. Application to the syntheses of phosphonate analogues of myoinositol, Phosph., Sulf. Silic., 109/110, 333, 1996. 

Treatment of pectin (containing 79. % of galacturonic acid) for 1 h at 121° gave 53.5% of galacturonic acid for a net recovery of 67%. The average of duplicate samples is presented. Amounts relative to myoinositol, the internal standard, in arbitrary units. 

A concise stereoselective synthesis of a myoinositol derivative has been achieved by ring-closing metathesis of diene 21 prepared from a readily available bis-Weinreb amide 20 of D-tartrate [Eq. (6.19)]. ... 

Miller has reported a minimal kinase for the phosphorylative enantioselective desymmetrization of a meio-inositol derivative. Peptide 132, identihed from a small library, provided the highest selectivity using the meso-tno 130 as substrate. This approach was applied to a hve-step synthesis of D-myoinositol-1-phosphate from readily available myoinositol ... 

This enzyme [EC 1.1.1.18] catalyzes the reaction of myoinositol with NAD+ to produce 2,4,6/3,5-pentahydroxy-cyclohexanone and NADH. 

This enzyme [EC 3.1.3.25], also referred to as myo-inosi-tol-l(or 4)-monophosphatase and myo-inositol-l-phos-phatase, catalyzes the hydrolysis of myo-inositol 1-monophosphate to generate myo-inositol and orthophosphate. Both enantiomers of myo-inositol 1-phosphate and myoinositol 4-phosphate can act as substrates. However, the enzyme does not hydrolyze inositol bisphosphates, tris-phosphates, or tetrakisphosphates. 

This enzyme [EC 3.1.3.26], also known as phytase, phy-tate 6-phosphatase, and myo-inositol-hexaphosphate 6-phosphohydrolase, catalyzes the hydrolysis of myoinositol hexakisphosphate to produce 1-myo-inositol... 

The major current working hypothesis for lithium s therapeutic mechanism of action supposes that its effects on phosphoinositol turnover, leading to an early relative reduction of myoinositol in human brain, are part of an initiating cascade of intracellular changes. Effects on specific isoforms of protein kinase C may be most relevant. Alterations of protein kinase C-mediated signaling alter gene expression and the production of proteins implicated in... 

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