Inositol and derivs

Hexanitroinositol. See under Inositol and Derivatives in this Vol Hexanitrosorbitol. See Sorbitol Hexanitrate under Sorbitol and Derivatives... 

This process (also known as the Ferrier II Reaction ) has proved to be of considerable value for the efficient, one-step conversion of 5,6-unsaturated hexopyranose derivatives into functionalized cyclohexanones useful for the preparation of such enantiomerically pure compounds as inositols and their amino, deoxy, unsaturated and selectively O-substituted derivatives, notably phosphate esters. In addition, the products of the carbocyclization have been incorporated into many complex compounds of interest in biological and medicinal chemistry. ... 

An additional action of Li" is interruption of the phosphatidylinositide cycle through an inhibitory action on inositol phosphate metabolism. By this mechanism, depletion of membrane inositol and the phosphoinosi-tide-derived second-messenger products diacylglycerol and inositol triphosphate ultimately reduces signaling through receptor systems dependent on the formation of these products. It is presently unclear to what extent inhibition of inositol phosphate metabolism contributes to the therapeutic properties of Li+ in bipolar patients. 

The capacity of inositol orthoformate derivatives 124 and 125 for binding to alkali metal ions was studied by electrospray ionization mass spectrometry (ESI-MS) gas-phase measurements <2001JOC8629>. The [5.5.5]-iono-phore 125 n = 3) possessed the highest Li /Na selectivity and the best affinity for Li. The results obtained proved to be in agreement with the size-fit concept. Other factors which influence the complexation are the orientation of the oxygen atoms, which are able to bind to metal, the basicity, and the polarizability of the heteroatoms around the perimeter of the binding cavity. 

Hexa-0-(trimethylsilyl)-mj/o-inositol is a solid,112 and this compound and the crystalline per(trimethylsilyl) ethers of scyllo-inositol and myo-inosose-2 have been fully characterized by Loewus,407 who has proposed these compounds as suitable internal standards. The scyllo- and myo-inositols, together with myo-inosose-2, have also been used in a study on the use of electron-capture detectors with trimethylsilyl derivatives.579... 

The inositol phosphates are linked into a metabolic cycle (Fig. 6.5) in which they can be degraded and regenerated. Via these pathways, the cell has the ability to replenish stores of inositol phosphate derivatives, according to demand. Ptdins may be regenerated from diacylglycerol via the intermediate levels of phosphatidic acid and CDP-glycerol. 

For the biosynthesis of inositols and of the benzene rings of aromatic a-amino acids nature employs nucleophilic centers at C-6 of a D-glucose-derived hexos-5-ulose phosphate [5] and at C-7 of a 3,7-dideoxyhept-2,6-diulosonic acid [6], respectively, ions 1 and 2... 

Table 5.21. 13C Chemical Shifts (5C in ppm) of Inositols and O-Methylated Derivatives [679],...

Tables II to X give the melting points and, where applicable, the optical rotations of the inositols, inososes, inosamines, and quercitols, and of all of their known O-substituted derivatives. Anhydroinositols, although not substitution products in the strict sense, are included, as are the carbonyl-functional derivatives of the inososes. Halogen- and nitro-substituted cyclitols, and the C-methyl-inositols and their derivatives, are not included most of these compounds are referred to in the text. The derivatives are arranged in the following order salts (inosamines) or functional derivatives (inososes), carboxylic esters, borates, nitrates, sulfonic esters, phosphates, glycosides, acetals (and Schiff bases), ethers (and IV-alkyl derivatives), and anhydrides.

Complexes of the ligand 1,3,5-triamino-1,3,5-trideoxy-cis-inositol and its derivatives. These ligands act as N3 donors towards both iron(II) and high-spin iron(III), although ring inversion could make a facially coordinating 03 donor set available (93,94). 

The cyclic nature of the nitrodesoxy inositols was demonstrated by the quantitative transformation of their pentaacetates to diacetyl-5-nitroresorcinol when treated with warm pyridine. Such ready aromati-zation is typical of the inositols and their derivatives. 

Analysis of the above product for carbon, hydrogen, nitrogen, inositol, and phosphorus gave values corresponding to the cyclohexylamine derivative. It had a melting point of 124-126°C. 

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