- Sulfonate protecting groups. Improved synthesis of scyllo-inositol and its orthoformate from myo-inositol
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A convenient high yielding method for the preparation of scyllo-inositol and its orthoformate from myo-inositol, without involving chromatography is described. myo-Inositol 1,3,5-orthoformate was benzoylated to obtain 2-O-benzoyl-myo-inositol 1,3,5-orthoformate. This diol was tosylated and the benzoyl group removed by aminolysis in a one-pot procedure to obtain 4,6-di-O-tosyl-myo-inositol 1,3,5-orthoformate. Swern oxidation of the ditosylate, followed by sodium borohydride reduction and methanolysis of tosylates gave scyllo-inositol 1,3,5-orthoformate (isolated as the triacetate). Aminolysis of the acetates followed by acid hydrolysis of the orthoformate moiety with trifluoroacetic acid gave scyllo-inositol in an overall yield of 64%.
- Sarmah, Manash P.,Shashidhar, Mysore S.
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- New conditions for the synthesis of scyllo-inositol starting from myo- inositol
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Equilibration of myo-inositol by Raney nickel in water has been reconsidered on a preparative scale. An efficient separation of scyllo- inositol by orthoacetate derivatization of the components of the crude mixture is proposed which gives the free scyllo-inositol in good yield.
- Husson, Christian,Odier, Leon,Vottero
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- Novel substrates for kinases involved in the biosynthesis of inositol pyrophosphates and their enhancement of atpase activity of a kinase
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IP6K and PPIP5K are two kinases involved in the synthesis of inositol pyrophosphates. Synthetic analogs or mimics are necessary to understand the substrate specificity of these enzymes and to find molecules that can alter inositol pyrophosphate synthesis. In this context, we synthesized four scyllo‐inositol polyphosphates—scyllo‐IP5, scyllo‐IP6, scyllo‐IP7 and Bz‐scyllo‐IP5—from myo-inositol and studied their activity as substrates for mouse IP6K1 and the catalytic domain of VIP1, the budding yeast variant of PPIP5K. We incubated these scyllo‐inositol polyphosphates with these kinases and ATP as the phosphate donor. We tracked enzyme activity by measuring the amount of radiolabeled scyllo‐inositol pyrophosphate product formed and the amount of ATP consumed. All scyllo‐inositol polyphosphates are substrates for both the kinases but they are weaker than the corresponding myo‐inositol phosphate. Our study reveals the importance of axial-hydroxyl/phosphate for IP6K1 substrate recognition. We found that all these derivatives enhance the ATPase activity of VIP1. We found very weak ligand‐induced ATPase activity for IP6K1. Benzoyl‐scyllo‐IP5 was the most potent ligand to induce IP6K1 ATPase activity despite being a weak substrate. This compound could have potential as a competitive inhibitor.
- Bhandari, Rashna,Ganguli, Shubhra,Madhusudhanan, Mithun C.,Manorama, Ruth,Mohanrao, Raja,Sureshan, Kana M.
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- COMPOSITION COMPRISING ISOMERS OF INOSITOL AND ITS USE
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A combination of scyllo-inositol and myo-inositol, wherein, the scyllo-inositol and myo-inositol are nutritional ingredients for use in the prevention or treatment of a condition selected from the group consisting of prediabetes, type II diabetes, gestational diabetes mellitus and a condition associated with any of the forgoing in a subject, and a composition comprising scyllo-inositol and myo-inositol.
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Page/Page column 2
(2020/03/15)
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- Method for Producing Scyllo-Inositol
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The disclosure provides a method of producing a scyllo-inositol or a new scyllo-inositol derivative in a one-step process, from ubiquitous and inexpensive raw materials. Also provided is a scyllo-inositol derivative bonded to saccharides such as glucose and similar.
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Paragraph 0188; 0189
(2015/01/06)
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- METHODS OF SYNTHESIS OF SCYLLITOL AND RELATED COMPOUNDS
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Methods of synthesis of scyllitol diborate and related compounds are provided, including methods that are performed in all-aqueous solutions. Also provided are methods in which the reaction products are recycled to increase the efficiency of the process. The methods include the steps of conversion of a solution of inositol to scyllitol, conversion of scyllitol in the solution to scyllitol diborate, and isolation of the scyllitol diborate from the solution. The scyllitol diborate is reacted to form substantially pure scyllitol diborate, and the remaining solution is efficiently recycled to scyllitol diborate, then to additional substantially pure scyllitol. This scyllitol diborate recycling step can be applied to a variety of processes to improve the yield of scyllitol. The methods are highly efficient and result in large scale reaction products of high purity.
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Page/Page column 58-61
(2012/05/04)
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- PROCESS FOR THE PREPARATION OF SCYLLO-INOSITOL
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This invention pertains to a process for manufacturing scyllo-Inositol. Specifically, the current invention pertains to a process for converting myo-Inositol to scyllo-Inositol using a bioconversion process.
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(2011/09/15)
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- ISOMERS OF INOSITOL NIACINATE AND USES THEREOF
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An ester formed from an inositol or an inositol derivative and niacin, wherein the inositol or the inositol derivatives comprises a stereoisomer selected from allo-inositol, cis-inositol, epi-inositol, muco-inositol, neo-inositol, scyllo-inositol, D-chiro-inositol and L-chiro-inositol, or pharmaceutically acceptable salts thereof. Examples of esters include inositol hexaniacinates such as allo-inositol hexaniacinate and cis-inositol hexaniacinate. The esters can be used to treat any disorder that is treatable with niacin therapy such as dyslipidemia, hypercholesterolemia, hyperlipidemia or cardiovascular disease. The esters can be administered with other agents such as HMG-CoA reductase inhibitors, statins, fibrates, activators of peroxisome proliferator activated receptors policosanol, phytosterols, tocotrienols, calcium, bile acid sequestrants, guar gum and free niacin. The invention includes pharmaceutical compositions containing these compounds.
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(2008/12/07)
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- PROCESS FOR PRODUCING SCYLLO-INOSITOL
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It is intended to provide a novel NAD+-independent myo-inositol 2-dehydrogenase which converts myo-inositol into scyllo-inosose in the absence of NAD+; a novel enzyme scyllo-inositol dehydrogenase which stereospecifically reduces scyllo-inosose into scyllo-inositol in the presence of NADH or NADPH; and a novel microorganism which belongs to the genus Acetobacter or Burkholderia and can convert myo-inositol into scyllo-inositol. By using these enzymes or the microorganism, scyllo-inositol is produced. Furthermore, scyllo-inositol is purified by adding boric acid and a metal salt to a liquid mixture containing scyllo-inositol and a neutral saccharide other than scyllo-inositol to form a scyllo-inositol/boric acid complex, separating the complex from the liquid mixture, dissolving the thus separated complex in an acid to give an acidic solution or an acidic suspension and then purifying scyllo-inositol from the acidic solution or the acidic suspension.
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- Stereoselective synthesis of myo-, neo-, L-chiro, D-chiro, allo-, scyllo-, and epi-inositol systems via conduritols prepared from p-benzoquinone
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A practical route is described for the flexible preparation of a wide variety of inositol stereoisomers and their polyphosphates. The potential of this approach is demonstrated by the synthesis of myo-, L-chiro-, D-chiro-, epi-, scyllo-, allo-, and neo-inositol systems. Optically pure compounds in either enantiomeric form can be prepared from p-benzoquinone via enzymatic resolution of a derived conduritol B key intermediate. High-performance anion-exchange chromatography with pulsed amperometric detection permits inositol stereoisomers to be resolved and detected with high sensitivity. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.
- Podeschwa, Michael,Plettenburg, Oliver,Vom Brocke, Jochen,Block, Oliver,Adelt, Stephan,Altenbach, Hans-Josef
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p. 1958 - 1972
(2007/10/03)
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- Novel synthesis of enantiomerically pure natural inositols and their diastereoisomers
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The various inositol polyphosphates have been found to trigger many important biological processes. Although the knowledge of this phosphoinositide signaling system has been discovered in the past 10 years, many factors remain unclear. For this reason, there is an increased demand for supplies of D-myo-inositol and particularly of novel analogues to investigate these biological mechanisms in more detail. Herein, we report the efficient syntheses of all diastereoisomers of inositol starting with 6-O-acetyl-5-enopyranosides. Conversion of 6-O-acetyl-5-enopyranosides into the corresponding substituted cyclohexanones (Ferrier-II rearrangement) was found to proceed efficiently with a catalytic amount of palladium dichloride. Stereoselective reduction of β-hydroxy ketones obtained provided the precursors to all inositol diastereoisomers in good to excellent yields and with high stereoselectivities. Good accessibility of these enantiomerically pure inositol diastereoisomers results in the efficient syntheses of D-myo-inositol 1,4,5-trisphosphate and D-myo-inositol 1,3,4,5-tetrakisphosphate.
- Takahashi,Kittaka,Ikegami
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p. 2705 - 2716
(2007/10/03)
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- Synthesis of all possible regioisomers of scyllo-inositol phosphate
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scyllo-Inositol is the all equatorial stereoisomer of myo-inositol. All possible 12 regioisomers of scyllo-inositol phosphate were synthesized for the first time via a scyllo-inositol benzoate intermediate, which was derived from a myo-inositol derivative. The stereoinversion of myo-inositol into scyllo-inositol was accomplished by Mitsunobu reaction of the vicinal cis- diol. The requisite intermediates, scyllo-inositol benzoates were obtained by benzoyl migration or random benzoylation, and phosphorylated to give scyllo- IP(n). (C) 1999 Elsevier Science Ltd.
- Chung, Sung-Kee,Kwon, Yong-Uk,Chang, Young-Tae,Sohn, Kwang-Hoon,Shin, Jung-Han,Park, Kyu-Hwan,Hong, Bong-Jin,Chung, In-Hee
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p. 2577 - 2589
(2007/10/03)
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- Transformation of cyclohexene to enantiopure cyclitols mediated by sequential oxyselenenylation with (S,S)-hydrobenzoin: Synthesis of D-chiro-inositol and muco-quercitol
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Oxyselenenylation of cyclohexene with (S,S)-hydrobenzoin and subsequent oxidation-elimination allows isolation of an allylic ether in which further phenylselenenylation is completely regioselective, thus allowing entry to the cyclitols D-chiro-inositol and muco-quercitol.
- Kim, Kwan Soo,Park, Jong H.,Moon, Hoi Kyung,Yi, Hann
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p. 1945 - 1946
(2007/10/03)
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- Microbial Oxidation of Aromatics in Enantiocontrolled Synthesis. Part 1.Expedient and General Asymmetric Synthesis of Inositols and Carbohydrates via and Unusual Oxidation of a Polarized Diene with Potassium Permanganate
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This paper reports on the details of a general design of carbohydrates and cyclitols from biocatalytically derived synthons.Homochiral 1-halogenocyclohexa-4,6-diene-2,3-diols 1a and 1b have been generated from chloro- and bromobenzene, respectively, by means of bacterial dioxygenase of Pseudomonas putida 39D.These chiral synthons have been manipulated to cyclitols and carbohydrates by further stereoselective functionalizations.The preperation of D-chiro-inositol, neo-inositol, muco-inositol, and allo-inositol exemplifies their use in enantiocontrolled synthesis.A novel oxidation of polarized dienes with KMnO4 resulted in the synthesis of α-halogeno epoxy diols, which proved unexpectedly stable.A mechanism is proposed for this transformation and placed in context with the only four reported examples of this reaction in the literature.In addition to the application of this new chemistry to the synthesis of cyclitols, chloro epoxy diol 21a has been transformed into a series of cyclitol synthons by reductive or hydrolytic operations.Reaction of 21a with ammonia led to the preparation of highly oxygenated pyrazines, whose structure were proven by X-ray crystallography.The use of 21a in the preparation of D-chiro-3-inosose, a hitherto unreported cyclitol derivative, is also reported.In addition, chloro epoxy diol 21a was transformed into D-erythruronolactone, completing the synthesis of this important chiral pool reagent in two operations from chlorobenzene.Oxidative cleavage of tetrol 20 yielded D-mannosolactone identical with an authentic sample.
- Hudlicky, Tomas,Mandel, Martin,Rouden, Jacques,Lee, Robert S.,Bachmann, Bryan,et al.
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p. 1553 - 1568
(2007/10/02)
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- General Synthesis of Inositols by Hydrolysis of Conduritol Epoxides Obtained Biocatalytically from Halogenobenzenes: (+)-D-chiro-Inositol, allo-Inositol, muco-Inositol and neo-Inositol
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Four of the nine isomeric inositols have been prepared by hydrolytic opening of epoxides derived from 3-halogenocyclohexa-3,5-diene-1,2-diol by further oxidation with potassium permanganate or by reduction of chiro-3-inosose (2L-2,3,6/4,5-pentahydroxycyclohexanone).
- Mandel, Martin,Hudlicky, Thomas
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p. 741 - 744
(2007/10/02)
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- GLYCOSYL-INOSITOL DERIVATIVES III. SYNTHESIS OF HEXOSAMINE-INOSITOL-PHOSPHATES RELATED TO PUTATIVE INSULIN MEDIATORS
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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.
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- Note on the Preparation of scyllo-Inositol
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A simplified synthesis of scyllo-inositol (4) from myo-inositol (1) via the pentaacetate of myo-inosose (3) is described.
- Kohne, Bernd,Praefcke, Klaus
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p. 866 - 868
(2007/10/02)
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- NOVEL BIOSYNTHESIS OF D-PINITOL IN SIMMONDSIA CHINENSIS
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Chase experiments with 14CO2 and feeding experiments with labwelled inositols showed that D-pinitol in leaves of Simmondsia chinensis arises via epimerization of D-ononitol.This finding represents an alternative pathway, since D-pinitol is formed in gymnosperms and other plants by epimerization of sequoyitol.Key Word Index -- Simmondsia chinensis; Simmondsiaceae; jojoba; biosynthesis; cyclitols; D-pinitol; D-ononitol.
- Dittrich, Peter,Korak, Andrea
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- Polyfunctionalised Cyclohexanes from Dianhydroinositols. cis-1,3(1,4)-Inosadiamines from Benzene
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The preparative value of the dianhydroinositols 4 - 6, which are readily available from benzene, for the total synthesis of cis-1,4- and cis-1,3-disubstituted cyclohexanetetrols is demonstrated.With monovalent reagents (H2O, HI, NaN3, NH2NH2) the twofold epoxide opening proceeds regioselectively (1,4-disubstitution) yielding the muco- and chiro-cyclohexane derivatives 9, 17, and 26.With hydrazine and N,N'-dimethylhydrazine as 1,2-dinucleophiles the cis-1,3-inosadiamines 7 g (5-epistreptamine) and 16 g, j (2-epistreptamine, actinamine) are obtained from 4/5 in good yields (75 - 90percent).From the less symmetrical 6, however, only the mixture of 25 g (streptamine) and 27 g is produced in modest yield (ca. 50percent).The epoxide opening reactions starting from 4 - 6 are kinetically so similar that a selective opening is not possible.
- Schubert, Juergen,Keller, Reinhold,Schwesinger, Reinhard,Prinzbach, Horst
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p. 2524 - 2545
(2007/10/02)
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- PURIFICATION AND STRUCTURE DETERMINATION OF THREE α-D-GALACTOPYRANOSYLCYCLITOLS FROM SOYA BEAN
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Three α-D-galactopyranosylcyclitols previously isolated from soya bean are shown to be 1D-2-O-(α-D-galactopyranosyl)-4-O-methyl-chiro-inositol, 1D-5-O-(α-D-galactopyranosyl)-4-O-methyl-chiro-inositol, and 1D-2-O-(α-D-galactopyranosyl)-chiro-inositol.Assignments of the (13)C-n.m.r. spectra of these compounds and of 1L-1-O-(α-D-galactopyranosyl)-myo-inositol (galactinol) are presented.The mass spectra of derivatives prepared by permethylation or perdeuteriomethylation, followed by hydrolysis and acetylation or methylation are discussed.
- Schweizer, Thomas F.,Horman, Ian
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