- Divergent synthesis of all possible optically active regioisomers of myo-inositol mono- and bisphosphates
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All possible optically active regioisomers of myo-inositol mono- and bisphosphates were synthesized using inositol derivatives suitably protected with various protecting groups (IRns) as key intermediates. A series of procedures including Novozym 435 cata
- Seo, Kyung-Chang,Yu, Seok-Ho,Chung, Sung-Kee
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p. 305 - 327
(2008/02/12)
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- Flexible stereo- and regioselective synthesis of myo-inositol phosphates (Part 2): Via nonsymmetrical conduritol B derivatives
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A practical route is described for the preparation of myo-inositol phosphates. Optically pure compounds can be prepared, in both forms, from p-benzoquinone by enzymatic resolution of a diacetoxyconduritol key intermediate. Monosubstituted inositol derivat
- Podeschwa, Michael A. L.,Plettenburg, Oliver,Altenbach, Hans-Josef
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p. 3116 - 3127
(2007/10/03)
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- Flexible stereo- and regioselective synthesis of myo-inositol phosphates (part 1): Via symmetrical conduritol B derivatives
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A practical route is described for the preparation of myo-inositol polyphosphates. Optically pure myo-inositol derivatives can be prepared from p-benzoquinone in both forms by enzymatic resolution of a C2- symmetric diacetoxyconduritol B key in
- Podeschwa, Michael A. L.,Plettenburg, Oliver,Altenbach, Hans-Josef
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p. 3101 - 3115
(2007/10/03)
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- An efficient route to optically active inositol derivatives via the resolution of myo-inositol 1,3,5-orthoformate: A short synthesis of D-myo-inositol-4-phosphate
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An efficient method for the resolution of myo-inositol 1,3,5-orthoformate has been developed. The triol, 1 was converted to diastereomers via reaction with (S)-O-acetylmandeloyl chloride. Conditions were optimized for a diastereomeric ratio of 7:3. Both t
- Sureshan, Kana M.,Watanabe, Yutaka
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p. 1193 - 1198
(2007/10/03)
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- Pathway of dephosphorylation of myo-inositol hexakisphosphate by phytases of legume seeds
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Using a combination of high-performance ion chromatography analysis and kinetic studies, the pathway of dephosphorylation of myo-inositol hexakisphosphate by the phytases purified from faba bean and lupine seeds, respectively, was established. The data demonstrate that the legume seed phytases under investigation dephosphorylate myo-inositol hexakisphosphate in a stereospecific way. The phytase from faba bean seeds and the phytase LP2 from lupine seeds degrade phytate by sequential removal of phosphate groups via D-Ins(1,2,3,5,6)P5, D-Ins(1,2,5,6)P4, D-Ins(1,2,6)P3, and D-Ins(1,2)P2 to finally Ins(2)P, whereas the phytases LP11 and LP12 from lupine seeds generate the final degradation product Ins(2)P via D-Ins(1,2,4,5,6)P5, D-Ins(1,2,5,6)P4, D-Ins(1,2,6)P3, and D-Ins(1,2)P2.
- Greiner, Ralf,Larsson Alminger, Marie,Carlsson, Nils-gunnar,Muzquiz, Mercedes,Burbano, Carmen,Cuadrado, Carmen,Pedrosa, Mercedes M.,Goyoaga, Carmen
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p. 6865 - 6870
(2007/10/03)
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- The pathway of dephosphorylation of myo-inositol hexakisphosphate by phytases from wheat bran of Triticum aestivum L. cv. Nourin #61
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Phytases are the primary enzymes responsible for the hydrolysis of phytic acid, myo-inositol-1, 2, 3, 4, 5, 6-hexakisphosphate (InsP6). The pathway of hydrolysis of InsP6 by phytase from wheat bran of Triticum aestivum L. cv. Nourin #61 is proved in this study. Structures of the intermediates were established by a variety of nuclear magnetic resonance techniques (1H-, two-dimensional 1H-1H coupling-correlation spectra and two-dimensional 31P-1H correlation spectra), gas chromatography, and bioassay. On the basis of the structures identified, initial hydrolysis of the phosphate ester occurs at the D/L-4 position of InsP6 to yield D/L-Ins (1, 2, 3, 5, 6) P5. After the dephosphorylation, the pathway of dephosphorylation is divided into two routes. The main route proceeds via D/L-Ins (1, 2, 5, 6) P4, D/L-Ins (1, 2, 6) P3 and D/L-Ins (1, 2) P2, while the minor route proceeds via D/L-Ins (1, 2, 3, 6) P4, Ins (1, 2, 3) P3 and D/L-Ins (1, 2) P2. D/L-Ins (1, 2) P2 is hydrolyzed at the D/L-1 or 2-position, and finally myo-inositol is produced.
- Nakano, Tadao,Joh, Toshio,Narita, Kazumasa,Hayakawa, Toshiro
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p. 995 - 1003
(2007/10/03)
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- myo-Inositol 1,4,5-Triphosphate and Related Compounds' Protonation Sequence: Potentiometric and 31P NMR Studies
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The protonation sequence of myo-inositol 1,4,5-triphosphate 3>, of its dehydroxylated analogue, Cyhx(1,2,4)P3, of two diphosphorylated inositol phosphates, Ins(1,4)P2 and Ins(4,5)P2 and of one inosit
- Schmitt, Laurent,Bortmann, Patrick,Schlewer, Gilbert,Spiess, B.
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p. 2257 - 2264
(2007/10/02)
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- Derivatives of cyclohexane
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New derivatives of cyclohexane in substantially pure form suitable as a pharmaceutical, foodstuff or as a stabilizer.
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- The synthesis of homochiral inositol phosphates from myo-inositol
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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-inosi
- Pietrusiewicz,Salamonczyk,Bruzik
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p. 5523 - 5542
(2007/10/02)
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- THE TOTAL SYNTHESIS OF myo-INOSITOL POLYPHOSPHATES
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Total synthesis of the individual enentiomers of myo-inositol 4-phosphate (15), myo-inositol 1,4-biphosphate (2) and myo-inositol 1,4,5-triphosphate (1), together with syntheses of racemic myo-inositol 1,3,4-triphosphate (4) and myo-inositol 2,4,5-triphos
- Vacca, Joseph P.,deSolms, S. Jane,Huff, Joel R.,Billington, David C.,Baker, Raymond,et al.
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p. 5679 - 5702
(2007/10/02)
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- The Total Synthesis of myo-Inositol Phosphates via myo-Inositol Orthoformate
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Novel selective alkylations of myo-inositol orthoformate (4) have been used to prepare a series of protected myo-inositol derivatives, (5a-e), (7), (10), (12), and (16).These intermediates have been used in efficient total syntheses of myo-inositol 2-phosphate, (9); myo-inositol 4-phosphate, (6); myo-inositol 1,3-bisphosphate, (18); and myo-inositol 1,3,4,5-tetrakisphosphate (14).This report represents the first total synthesis of the important natural metabolites (14) and (18) and significantly improved methods of preparation of (6) and (9).
- Billington, David C.,Baker, Raymond,Kulagowski, Janusz J.,Mawer, Ian M.,Vacca, Joseph P.,et al.
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p. 1423 - 1429
(2007/10/02)
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- Highly Efficient Protection by the Tetraisopropyldisiloxane-1,3-diyl Group in the Synthesis of myo-Inositol Phosphates as Inositol 1,3,4,6-tetrakisphosphate
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Regioselective introduction of the tetraisopropyldisiloxane-1,3-diyl group onto myo-inositol and 1,2-O-cyclohexylidene-myo-inositol realised the efficient synthesis of various myo-inositol phosphates.
- Watanabe, Yutaka,Mitani, Motohiro,Morita, Takao,Ozaki, Shoichiro
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p. 482 - 483
(2007/10/02)
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- Phosohoranylation de polyols: Voie d'acces aux phosphates d'interet biologique. I. Cas du myo-inositol
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An original method for the phosphorylation of an unprotected myo-inositol is described, which yields several myo-inositol phosphates at the same time.The reaction proceeds via a partial or complete phosphoranylation of the cyclitol by means of the aminobicyclophosphane 8, followed by oxidation of the resulting bicyclophosphoranes bearing a P-H bond and acid hydrolysis of the neutral phosphates thus formed.In the case of the tris-phosphoranylation we identified, among the HPLC fractions, the myo-inositol-1,2-(cycl)phosphate 22, the myo-inositol-1-phosphate 23, and the myo-inositol-2-phosphate 24.
- Duthu, Brigitte,Houalla, Douraid,Wolf, Robert
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p. 2965 - 2974
(2007/10/02)
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- Synthesis of myo-Inositol 1-Phosphate and 4-Phosphate, and of their Individual Enantiomers
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New methodology is described which allows the synthesis of myo-inositol 1-phosphate completely free of contamination by the 2-isomer, and novel resolution procedures have been developed for the preparation of the enantiomers of myo-inositol 1- and 4-phosp
- Billington, David C.,Baker, Raymond,Kulagowski, Janusz J.,Mawer, Ian M.
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p. 314 - 316
(2007/10/02)
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