- Inositol Biotransformation
-
Disclosed is a method of preparing pure or substantially pure D-myo-inositol-3-phosphate from glucose-6-phosphate and/or fructose-6-phosphate. The method may also be applied to protected and/or derivative forms of glucose-6-phosphate and/or fructose-6-phosphate so as to form protected/derivative forms of D-myo-inositol-3-phosphate, for use in further chemical reactions. The enzyme D-myo-inositol-3-phosphate synthase (INO1) is contacted with the glucose-6-phosphate and/or fructose-6-phosphate to generate labeled or unlabeled, protected or unprotected D-myo-inositol-3-phosphate, which may be further reacted and/or purified.
- -
-
Paragraph 0071
(2016/07/05)
-
- Divergent synthesis of all possible optically active regioisomers of myo-inositol mono- and bisphosphates
-
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
-
p. 305 - 327
(2008/02/12)
-
- Flexible stereo- and regioselective synthesis of myo-inositol phosphates (part 1): Via symmetrical conduritol B derivatives
-
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
-
p. 3101 - 3115
(2007/10/03)
-
- Pathway of dephosphorylation of myo-inositol hexakisphosphate by phytases of legume seeds
-
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
-
p. 6865 - 6870
(2007/10/03)
-
- Enantiodivergence in small-molecule catalysis of asymmetric phosphorylation: Concise total syntheses of the enantiomeric D-myo-inositol-1-phosphate and D-myo-inositol-3-phosphate
-
Peptide-based catalysts have been found that catalyze the enantiodivergent phosphorylation of a meso myo-inositol-derived triol (1). The sequential screening of random peptide libraries, followed by the evaluation of a focused library, led to the identifi
- Sculimbrene, Bianca R.,Morgan, Adam J.,Miller, Scott J.
-
p. 11653 - 11656
(2007/10/03)
-
- The pathway of dephosphorylation of myo-inositol hexakisphosphate by phytases from wheat bran of Triticum aestivum L. cv. Nourin #61
-
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
-
p. 995 - 1003
(2007/10/03)
-
- Structure of (±)-1,2;4,5-di-o-cyclohexylidene myo-inositol and synthesis of myo-inositol 3-phosphate via its phosphorylation with (2R,4S,5R)-2-chloro-3,4-dimethyl-5-phenyl-1,3,2-oxazaphospholidin-2-one
-
The crystal structure of (±)-1,2;4,5-di-O-cyclohexylidene myo-inositol, refined to R = 2.9%, shows interestingly disordered (flip-flop) hydrogen bonding. The higher reactivity of the 1/3 positions (rather than 4/6) has been evaluated using semi-empirical calculations. This diol has been phosphorylated with (2R,4S,5R)-2-chloro-3,4-dimethyl-5-phenyl-1,3,2- oxazaphospholidin-2-one and the diastereoisomer derived from phosphorylation at the 3-position was isolated by crystallisation. Deprotection with TFA/H2O then H2/Pd-C afforded myo-inositol 3-phosphate in only four steps from myo- inositol.
- Spiers, Ian D.,Schwalbe, Carl H.,Blake, Alexander J.,Solomons, Kevin R.H.,Freeman, Sally
-
-
- myo-Inositol 1,4,5-Triphosphate and Related Compounds' Protonation Sequence: Potentiometric and 31P NMR Studies
-
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.
-
p. 2257 - 2264
(2007/10/02)
-
- Derivatives of cyclohexane
-
New derivatives of cyclohexane in substantially pure form suitable as a pharmaceutical, foodstuff or as a stabilizer.
- -
-
-
- Synthesis of D-myoinositol-1-phosphate
-
A method of synthesizing D-myoinositol-1-phosphate from 1,2-(R1)-3-R2 -myoinositol compounds of the formula STR1 wherein R1 is a bridging type protective group bonded to two oxygen atoms at the 1- and 2-position, and R2 is a protective group coupled to the oxygen atom at the 3-position. D-Myoinositol-1-phosphate is useful as an intermediate for the production of inositol-1,4,5-triphosphate.
- -
-
-
- The synthesis of homochiral inositol phosphates from myo-inositol
-
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
-
p. 5523 - 5542
(2007/10/02)
-
- GLYCOSYL-INOSITOL DERIVATIVES III. SYNTHESIS OF HEXOSAMINE-INOSITOL-PHOSPHATES RELATED TO PUTATIVE INSULIN MEDIATORS
-
The disaccharides related to glycosyl phosphatidyl inositol anchors of membrane proteins, 4-O-(2-amino-2-deoxy-α-D-glucopyranosyl)-D-myo-inositol-1-phosphate and 4-O-(2-amino-2-deoxy-α-D-galactopyranosyl)-D-chiro-inositol-1-phosphate, have been prepared from optically resolved myo-inositol derivatives.The chiro-inositol moiety was obtained by epimerization of a selectively blocked myo-inositol-triflate ester.The resolved inositols were subsequently phosphorylated to yield the disaccharide aglycones.The amino-sugar components were prepared by azidonitration of suitably protected glucal and galactal derivatives.The derived pyranosyl chlorides were then condensed with the inositol phosphates using silver triflate as the promoter.
- Berlin, William K.,Zhang, Wen-Sheng,Shen, T. Y.
-
-
- Myo-inositol orthoformates
-
This invention provides the 4-mono-anion of myo-inositol orthoformate, and describes a process for preparing this anion as well as the use of this anion in the preparation of a variety of mono- and poly-phosphate derivatives of myo-inositol.
- -
-
-
- The Total Synthesis of myo-Inositol Phosphates via myo-Inositol Orthoformate
-
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.
-
p. 1423 - 1429
(2007/10/02)
-
- Highly Efficient Protection by the Tetraisopropyldisiloxane-1,3-diyl Group in the Synthesis of myo-Inositol Phosphates as Inositol 1,3,4,6-tetrakisphosphate
-
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
-
p. 482 - 483
(2007/10/02)
-
- Phosohoranylation de polyols: Voie d'acces aux phosphates d'interet biologique. I. Cas du myo-inositol
-
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
-
p. 2965 - 2974
(2007/10/02)
-
- Synthesis of myo-Inositol 1-Phosphate and 4-Phosphate, and of their Individual Enantiomers
-
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.
-
p. 314 - 316
(2007/10/02)
-