Myo-inositol 1-phosphate

Volume 26 myo-Inositol Phosphates, Phosphoinositides, and Signal Transduction... 

Choi, G. Chang, Y.-T. Chung, S.-K. Choi, K.Y. Molecular interactions of all possible regioisomers of synthetic myo-inositol phosphates with inositol... 

On hydrolysis of the phosphatides, myo-inositol monophosphate—and, from a brain phosphatide, a diphosphate—is obtained but, these products have, in most cases, not been adequately characterized, and it is not yet known whether all phospholipids contain the same myo-inositol phosphate. It has been shown169-170 that the phosphate obtained by hydrolysis of liver phosphatide171 or soybean phosphatide172 is a mixture of myo-inositol 1- and 2-phosphates. A myo-inositol phosphate, of unknown constitution, was isolated173 from liver without previous hydrolysis apparently it occurs in the free state. 

Protection of diols. The reaction of diols with 1 and pyridine provides protected derivatives, which are cleaved by aqueous HF or R3NHF. These disiloxane derivatives are exceedingly useful for preparation of myo-inositol phosphates.2 Thus... 

Grado, C. and Ballou, C. E. (1960) Myo-inositol phosphates from beef brain phospho-inositide, J. Biol. Chem. 235, PC23-24. 

Biswas, B.B., Biswas, S., Chakrabarti, S., and De, B.P., 1978a, A novel metabolic cycle involving myo-inositol phosphates during formation and germination of seeds. In Wells, W.W. and Eisenberg, E, Jr. (eds.), Cyclitols and Phosphoinositides. Academic Press, New York, pp. 57-68. 

Laussmann, T., Pikzack, C., Thiel, U., Mayr, G.W., and Vogel, G., 2000, Diphospho-myo-inositol phosphates during the life cycle of Dictyostelium and Polysphondylium. Eur. J. Biochem. 267 2447-2451. 

Martins, L.O., Carreto, L.S., Da Costa, M.S., and Santos, H., 1996, New compatible solutes related to di-myo-inositol-phosphate in members of the order Thermotogales. J. Bacteriol. 178 5644-5651. 

Kniewel, R., Buglino, J.A., Shen, V, Chadya, T., Beckwith, A., and Lima, C.D., 2002, Structural analysis of Saccharomyces cerevisiae myo-inositol phosphate synthase. J. Struct. Funct. Genomics2 129-134. 

Smart, C.C., and Fleming, A.J., 1993, A plant gene with homology to D-myo-inositol-phosphate synthase is rapidly and specially upregulated during an abscsic acid induced response in Spirodelapolyrrihiza. Plant J. 4 279-293. 

In order to clarify the metabolic pathways for substituted myo-inositols (in practice myo-inositol phosphates), the lowest-locant rule, which gives priority to a In-locant has been relaxed, and numbering based on the lo-series is now allowed (Biochem. J., 258, 1-2, 1989). This is to allow substances related by simple chemical or biochemical transformations to carry the same labels. Thus, iL-myo-inositol 1-phosphate may now be called lD-myo-inositol-3-phosphate. 

Eukaryotic peptide chain elongation factor-2 Triosephosphate isomerase Myo-inositol-phosphate synthase Mannose-1-phosphate guanylj transferase Alcohol dehydrogenase Aldehyde reductase Ade5... 

In tervalent phosphorus acid chemistry the main area of activity has again been the use of tervalent phosphorus acid derivatives for the preparation of phosphates or modified phosphates of biochemical interest. Apart from the nucleotide field, vide infra), pentavalent phosphorus acid chemistry seems to be mainly in the doldrums exceptions to this are the areas of myo-inositol phosphate and aminoalkylphosphonate chemistry where activity remains high. 

This protocol can be applied to the 6-0-acetyl-5-enopyranoside 229 with good efficiency and the utility is well demonstrated by the synthesis of the D-myo-inositol phosphate, IP3 [193,194],... 

Pizzarello S, Weber AL (2010) Stereoselective syntheses of pentose sugars under realistic prebiotic conditions. Orig Life Evol Biosph 40 3-10 Powner MW, Garland B, Sutherland JD (2009) Synthesis of activated pyrimidine ribonucleotides in prebiotically plausible conditions. Nature 459 239-242 Scumlimbrene BR, Miller SJ (2001) Discovery of a catalytic asymmetric phosphorylation through selection of a minimal kinase mimic a concise total synthesis of D-myo-inositol-phosphate. J Am Chem Soc 123 10125-10126... 

Burmester, A. and Jastorff, B. (1996) Enantiosepara-tion in the synthesis of myo-inositol phosphates by high-performance liquid chromatography using a (3-cyclodextrin-bonded column, yourna/ of Chromatography A 749, 25-32. 

Patthy, M., Balia, T. and Aranyi, P. (1990) High-performance reversed-phase ion-pair chromatographic study of myo-inositol phosphates separation of myo-inositol phosphates, some common nucleotides and sugar phosphates. Journal of Chromatography A 523, 201-21 5. 

RICE ORYZA SATIVA L.) The activity of the add phosphatase purified from the aleurone particle of rice was assessed using various substrates para-nitrophenyl phosphate was readily hydrolysed, as were adenosine triphosphate and pyrophosphate. Among the myo-inositol phosphates, inositol trisphos-phate was hydrolysed at the highest rate (29% of para-nitrophenyl phosphate). The enzyme was also characterized by low or little activity towards (3-glycerophosphate, glucose 6-phosphate and nucleotide phosphates (Yamagata et al, 1980). 

Cario, A., Mizgier, A., Thiel, A., Jebbar, M., and Oger, P.M. (2015) Restoration of the di-myo-inositol-phosphate pathway in the piezo-hyperthermophilic archaeon Ihermococcus barophilus. Biochimie, 118, 286-293. 

Esteves, A.M., Chandrayan, S.K., McTernan, P.M., Borges, N., Adams, M.W.W., and Santos, H. (2014) Man-nosylglycerate and di-myo-inositol phosphate have interchangeable roles during adaptation of Pyrococcus furiosus to heat stress. Appl Microbiol Biotechnol, 80, 4226-4233. 

X, Atomi, H., and Santos, H. (2009) Jhermococcus kodakaremis mutants deficient in di-myo-inositol phosphate use aspartate to cope with heat stress. /. Bacterial, 192,191-197. 

Cyclitols and Derivatives. - A review on the application of the Pd(II)-catalysed Ferrier (II) carbocyclization in the synthesis of p-glucosidase inhibitors, cyclophellitol, all the diastereoisomers of inositol, and D-myo-inositol phosphates has been published. ... 

Two synthetically in iortant variants of the Ferrier carbocyclization reaction have been reported. One is a rearrangement of enol acetate 24 (Scheme 12.7). Reaction of 24 with a stoichiometric amount of Hg salt afforded an organomercurial intermediate 25, which was then treated with NaCl to induce the cyclization affording inosose derivatives 26a and 26b with good stereoselectivity. As biologically inportant myo-inositol derivatives, such as d-myo-inositol phosphates, are optically active, the enol-acetate version of the Ferrier carbocyclization would be effective for the preparation of enantiomerically pure inositol derivatives. 

Billington DC, Baker R, Kulagowski JJ, Mawer IM, Vacca JP, deSolms SJ, Huff JR (1989) The total synthesis of myo-inositol phosphates via myo-inositol orthoformate. J Chem Soc Perkin Trans 1 1423-1429... 

Morgan AJ, Wang YK, Roberts MF, Miller SJ (2004) Chemistry and biology of deoxy-myo-inositol phosphates stereospecificity of substrate interactions within an archaeal and a bacterial IMPase. J Am Chem Soc 126 15370-15371... 

The catabolites of phytase activity in wheat are myo-inositol, phosphate, and the macroelements potassium, magnesium and calcium. Myo-inositol phosphate ester intermediates with fewer than six phosphate groups do not accumulate within the grain during hydrolysis of the phytin molecule [94], which is indicative of its rapid and complete breakdown by phytases. Movement of the catabolites from the aleurone layer and their redistribution into the developing seedling appears to be by simple diffusion through the endosperm, without any apparent competition for uptake by the scutellum. 

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