- Incorporation of a fluorous diazirine group into phosphatidylinositol 4,5-bisphosphate to illustrate its interaction with ADP-ribosylation factor 1
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Phosphatidylinositides are one family of the most versatile signaling molecules in cells, yet how they interact with different proteins to regulate biological processes is not well understood. Towards a general strategy to identify phosphatidylinositide-protein interactions, a fluorous diazirine group has been incorporated into phosphatidylinositol 4,5-bisphosphate (PIP 2). The modified PIP2 was effectively cleaved by phospholipase C, one signaling protein that utilizes PIP2 as its endogenous substrate. Upon light illumination, the PIP2 probe effectively crosslinks with small GTPase ADP-ribosylation 1 to form a complex, suggesting that the probe might be suitable to identify PIP2- interacting proteins on the proteome level. The Royal Society of Chemistry 2012.
- Huang, Weigang,Sun, Wei,Song, Zhiquan,Yu, Yanbao,Chen, Xian,Zhang, Qisheng
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body text
p. 5197 - 5201
(2012/08/08)
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- FLUOROGENIC SENSORS FOR PHOSPHOLIPASE C ISOZYMES
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The present invention provides fluorogenic substrates and methods of use in detecting and analyzing phospholipase C isozyme (PLC) activity.
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Page/Page column 28; 34
(2012/01/05)
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- Synthesis of unsaturated phosphatidylinositol 4,5-bisphosphate and analogues
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A new approach for the synthesis of phosphatidylinositol 4,5-bisphosphate [PtdIns(4,5)P2] is described, compatible with unsaturated fatty acid esters, as well as phosphorothioate and acetylenic analogues. This strategy depends on masking the ph
- Panchal, Nitesh,Gaffney, Piers R. J.
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experimental part
p. 4832 - 4841
(2010/02/16)
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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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- Divergent syntheses of all possible optically active regioisomers of myo-inositol tris- and tetrakisphosphates
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Since the discovery of D-myo-inositol 1,4,5-trisphosphate, which plays a pivotal role as a second messenger in transmembrane signaling, the scope of the phosphoinositide-based signaling processes has been continually expanding. However, the clear understanding of the molecular signal transduction mechanisms including the functions of newly found IPn is still lacking. As a continuing effort to our previously reported syntheses of all possible 39 optically inactive regioisomers of myoinositol phosphates (IPn; n = 1-6), we synthesized all possible optically active regioisomers of myo-IP3 and myo-IP4 using chiral IBz3s and IBz2s, respectively. A series of procedures involving CRL-catalyzed enzymatic resolution of racemic 1,2:5,6-di-O-isopropylidene-myo-inositol and base-catalyzed benzoyl migration in tri- and dibenzoyl-isopropylidene-myo-inositol afforded eight enantiomeric pairs of IBz3 and six enantiomeric pairs of IBz2, respectively. Phosphorylation of these intermediates by the phosphitylation and oxidation procedure gave the target products.
- Chung, Sung-Kee,Kwon, Yong-Uk,Shin, Jung-Han,Chang, Young-Tae,Lee, Changgook,Shin, Boo-Gyo,Kim, Kyung-Cheol,Kim, Mahn-Joo
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p. 5626 - 5637
(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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- Novel synthesis of enantiomerically pure natural inositols and their diastereomers
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A novel synthesis of all stereoisomers of natural inositols has been developed. The key strategy is the stereoselective reduction of substituted β-hydroxy cyclohexanones which are prepared from a variety of 6-O-acetyl 5- enopyranosides via Ferrier-II reaction catalyzed by palladium chloride. The utility of this approach is demonstrated by the synthesis of D-myo-inositol 1,4,5-tris(phosphate)(IP3).
- Takahashi, Hideyo,Kittaka, Hisae,Ikegami, Shiro
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p. 9707 - 9710
(2007/10/03)
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- Rapid and practical synthesis of D-myo-inositol 1,4,5-trisphosphate
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A concise synthetic sequence to biologically active O-myo-inositol 1,4,5-trisphosphate is described involving just five steps from myo-inositol and minimal chromatography with a key transformation of orthoacetate into acetate protection.
- Garrett, Shane W.,Liu, Changsheng,Riley, Andrew M.,Potter, Barry V. L.
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p. 1367 - 1368
(2007/10/03)
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- A convenient synthesis of D-myo-inositol 1,4,5-trisphosphate (Ins(1,4,5)P3) and L-myo-inositol 1,4,5-trisphosphate (Ins(3,5,6)P3)
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An efficient synthesis of an optically active inositol derivative that is a precursor to D-myo-inositol 1,4,5-trisphosphate (Ins(1,4,5)P3, (-)) is described. Crystallization of the diastereomers of (±) -1-O-[(+)- menthoxycarbonyl]-6-O-benzyl-2,3:4,5-di-O-isopropylidene-myo-inositol diastereomers from methanol gives only one diastereomer. Alkaline hydrolysis gives the useful inositol derivative (-)-6-O-benzyl-2,3:4,5-di-O- isopropylidene-myo-inositol. Likewise, crystallization of the diastereomers of (±)-3-O-[(-)-menthoxycarbonyl]-4-O-benzyl-1,2:5,6-di-O-isopropylidene- myo-inositol from methanol gave a pure compound which could be hydrolyzed to give (+)-4-O-benzyl-1,2:5,6-di-O-isopropylidene-myo-inositol, a precursor to D-myo-inositol 3,5,6-trisphosphate (Ins(3,5,6)P3, (+)). The ease with which these enantiomerically pure inositol derivatives were isolated may facilitate the synthesis of more complex inositol phosphate derivatives such as D-myo- inositol 1,3,4,5-tetrakisphosphate.
- Leung, Lawrence W.,Bittman, Robert
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p. 171 - 179
(2007/10/03)
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- Modulation of the inositol 1,4,5-trisphosphate receptor by inositol phosphates
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The mode of recognition at the binding site of the Ins(1,4,5)P3 receptor was assessed by examining the structure-activity relationships of different Ca2+-mobilizing inositol phosphates.
- Lu, Pei-Jung,Chen, Ching-Shih
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p. 325 - 328
(2007/10/03)
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- Unambiguous Total Synthesis of the Enantiomers of myo-Inositol 1,3,4-Trisphosphate: 1L-myo-Inositol 1,3,4-Trisphosphate Mobilizes Intracellular Ca2+ in Limulus Photoreceptors
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Syntheses of the enantiomers of myo-inositol 1,3,4-trisphosphate are described. 1,4-Di-O-allyl-myo-inositol was regioselectively p-methoxybenzylated at the 3-position to give 1,4-di-O-allyl-3-O-(p-methoxybenzyl)-myo-inositol followed by benzylation of the remaining free hydroxyl groups to give the key intermediate 1,4-di-O-allyl-2,5,6-tri-O-benzyl-3-O-(p-methoxybenzyl)-myo-inositol.Removal of the p-methoxybenzyl and allyl groups gave 2,4,5-tri-O-benzyl-myo-inositol which was-phosphitylated with bis(benzyloxy)(diisopropylamino)phosphine to give the fully protected trisphosphite triester.Oxidation using tert-butyl hydroperoxide gave 2,5,6-tri-O-benzyl-1,3,4-tris(dibenzylphospho)-myo-inositol, and deprotection using sodium in liquid ammonia gave racemic myo-inositol 1,3,4-trisphosphate.Deprotection of the key intermediate 1,4-di-O-allyl-2,5,6-tri-O-benzyl-3-O-(p-methoxybenzyl)-myo-inositol by isomerization of allyl groups followed by mild acid hydrolysis gave 2,4,5-tri-O-benzyl-1-O-(p-methoxybenzyl)-myo-inositol, which was converted to the diastereoisomeric bis-(-)-camphanates.The diastereoisomers were separated by column chromatography and the camphanates and the p-methoxybenzyl group removed by saponification and acid hydrolysis, respectively, for each diastereoisomer to give the enantiomers of 2,4,5-tri-O-benzyl-myo-inositol.The absolute configurations of the latter were established by conversion of 1L-2,5,6-tri-O-benzyl-3-O-(p-methoxybenzyl)-myo-inositol to the known 1L-1,2,4,5,6-penta-O-benzyl-myo-inositol.Phosphorylation and deblocking gave the D- and L-enantiomers of myo-inositol 1,3,4-trisphosphate.Biological evaluation in Limulus photoreceptors showed that 1L-myo-inositol 1,3,4-trisphosphate was much more active than the D-enantiomer, producing repetitive bursts of depolarization due to mobilization of intra cellular calcium.
- Riley, Andrew M.,Payne, Richard,Potter, Barry V. L.
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p. 3918 - 3927
(2007/10/02)
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- SYNTHESIS, POTENTIOMETRIC AND 31P-NMR INVESTIGATIONS OF THE IONIZATION STATE AND COMPLEXATION PROPERTIES OF INOSITOL-PHOSPHATES: BIOLOGICAL CONSEQUENCES
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The synthesis and the potentiometric studies of inositol-phosphates allow, particularly for Ins(1,4,5)P3, the correlation between the ionization state of the phosphate functions and the binding properties of the inositol-phosphates.
- Schmitt, Laurent,Bortmann, Patrick,Spiess, Bernard,Schlewer, Gilbert
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p. 147 - 150
(2007/10/02)
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- Enzyme aided synthesis of D-myo-inositol 1,4,5-trisphosphate
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Racemic 2,3-mono-O-cyclohexylidene-myo-inositol (1) was efficiently resolved by enzymatic esterification in organic solvent and a new practical route for synthesis of D-myo-inositol 1,4,5-trisphosphate (13) started from the optically pure D-2,3-mono-O-cyclohexylidene-myo-inositol (3) is described.
- Ling, Lei,Ozaki, Shoichiro
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p. 2501 - 2504
(2007/10/02)
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- The regioselective synthesis of enantiomerically pure myo-inositol derivatives. Efficient synthesis of myo-inositol 1,4,5-trisphosphate
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Regioselective 1-O-acylation of myo-inositol and simultaneous optical resolution has been achieved by perborylation, transmetallation using di-n-butyltin-bis-acetylacetonate and then acylation with (-)-menthyl chloroformate. Diastereomerically pure 1-O-(-
- Aguilo, Agustin,Martin-Lomas, Manuel,Penades, Soledad
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p. 401 - 404
(2007/10/02)
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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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- Syntheses of D-myo-inositol 1,4,5-trisphosphate affinity ligands
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A mixture of 2,3,6-tri-O-benzoyl-4,5-di-O-benzyl-D-myo-inositol and 1,3,6-tri-O-benzoyl-4,5-di-O-benzyl-D-myo-inositol, obtained during our synthesis of D-myo-inositol 1,4,5-trisphosphate C.E.Ballou and W.Tegge, Proc.Natl.Acad.Sci.U.S.A., 86 (1989) 94-98
- Tegge, Werner,Ballou, Clinton E.
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- Practical Synthesis of Enantiomerically Pure myo-Inositol Derivatives
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The synthesis of enantiomerically pure myo-inositol derivatives is accomplished using a mandelic acid-derived acyl protecting group.
- Bruzik, Karol S.,Myers, Jeffrey,Tsai, Ming-Daw
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p. 1009 - 1012
(2007/10/02)
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- Expedient Synthesis of D-myo-Inositol 1,4,5-Trisphosphate and D-myo-Inositol 1,4-Bisphosphate
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Readily available selfresolving myo-inositol D-camphor 2,3-monoacetal is converted into the title inositol phosphates by the concise procedures utilizing 1,4,5-selective tris-acylation and 1,4-selective bis-silylation of the starting tetrol in the key ste
- Salamonczyk, Grzegorz M.,Pietrusiewicz, K. Michal
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p. 6167 - 6170
(2007/10/02)
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- A Short Step Synthesis of Optically Active myo-Inositol 1,3,4,5-Tetrakis(phosphate) and myo-Inositol 1,4,5-Tris(phosphate) from 1,3,5-Tri-O-benzoyl-myo-inositol
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A short and practical synthesis of myo-inositol 1,3,4,5-tetrakis(phosphate) and myo-inositol 1,4,5-tris(phosphate) has been achieved by direct benzoylation of myo-inositol, enantioselective tartaroylation and removal of acyl protecting groups with Grignar
- Watanabe, Yutaka,Fujimoto, Takahiro,Shinohara, Tomoichi,Ozaki, Shoichiro
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p. 428 - 429
(2007/10/02)
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- MICROBIAL OXIDATION IN SYNTHESIS: PREPARATION OF MYO-INOSITOL PHOSPHATES AND RELATED CYCLITOL DERIVATIVES FROM BENZENE.
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Pseudomonas putida oxidation of benzene affords cis-3,5-cyclohexadiene-1,2-diol (2) which is used as a novel precursor for the synthesis of D- and L-myo-inositol 1,4,5-triphosphates, (-)-(1) and (+)-(1).The versatility of this approach to functionalised cyclitols is illustrated in the synthesis of myo-inositol 1-phosphate (19), 6-deoxy, 6-deoxy-6-fluoro, and 6-deoxy-6-methyl myo-inositols (31), (37) and (43), and their 1,4,5-trisphosphate derivatives (33), (39) and (45).
- Ley, Steven V.,Parra, Margarita,Redgrave, Alison J.,Sternfeld, Francine
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p. 4994 - 5026
(2007/10/02)
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- Total synthesis of myo-inositol polyphosphates from benzene via conduritol B derivatives
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The four (±)-myo-inositol phosphates 1,4,5-IP3 (1), 2,4,5-IP3 (15), 1,2,4,5-IP4 (17) and 4,5-IP2 (19) have been synthesised from benzene, using the protected conduritol B (10) as the key intermediate.
- Carless, Howard A. J.,Busia, Kofi
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p. 3449 - 3452
(2007/10/02)
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- TOTAL SYNTHESIS OF chiro-INOSITOL 2,3,5-TRISPHOSPHATE: A myo-INOSITOL 1,4,5-TRISPHOSPHATE ANALOGUE FROM BENZENE VIA PHOTO-OXIDATION
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The inositol tris- and tetrakis-phosphate analogues (4) and (14) have been synthesized from benzene by a sequence including reaction of singlet oxygen with a trans-cyclohexa-3,5-diene-1,2-diol (3) derivative.
- Carless, Howard A. J.,Busia, Kofi
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p. 1617 - 1620
(2007/10/02)
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- An efficient phosphorylation method using a new phosphitylating agent, 2-diethylamino-1,3,2-benzodioxaphosphepane
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A variety of alcohols containing polyols like inositol derivatives were efficiently phosphitylated by the reaction with 2-diethylamino-1,3,2-benzodioxaphosphepane in the presence of tetrazole and the resulting phosphites were oxidized with mCPBA or sulfur to yield the corresponding phosphates or thiophosphates in excellent yields.
- Watanabe,Komoda,Ebisuya,Ozaki
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p. 255 - 256
(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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- TOTAL SYNTHESES OF CHIRAL sn-myo-INOSITOL-1,4,5-TRISPHOSPHATE AND ITS ENANTIOMER.
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sn-myo-Inositol-1,4,5-trisphosphate (Ins(1,4,5)P3) and its enantiomers are prepared by synthesis of suitably protected myo-inositols, separation of enantiomers via the formation of D-mannose diastereomeric derivatives and selective phosphorylations.
- Stepanov, Alexander E.,Runova, Olga B.,Schlewer, Gilbert,Spiess, Bernard,Shvets, Vitaly I.
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p. 5125 - 5128
(2007/10/02)
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- AN EFFICIENT SYNTHESIS OF OPTICALLY ACTIVE D-MYO-INOSITOL 1,4,5-TRIPHOSPHATE
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An effective synthesis of D-myo-inositol 1,4,5-triphosphate was developed using a chiral inositide precursor which can be prepared via a facile enzymatic or chemical method.
- Liu, Yeuk-Chuen,Chen, Ching-Shih
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p. 1617 - 1620
(2007/10/02)
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- Enantiospecific Synthesis of D-myo-Inositol 1,4,5-Trisphosphate from (-)-Quinic Acid
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A versatile, enentiospecific approach to functionalized cyclitols from (-)-quinic acid is illustrated by a synthesis of D-myo-inositol 1,4,5-trisphosphate, the calcium-mobilizing intracellular second messenger of the phosphatidylinositol cycle.
- Falck, J. R.,Yadagiri, Pendri
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p. 5851 - 5852
(2007/10/02)
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- Intermediate compounds resulting from method for forming a dihydrogen-phosphate inositol
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This invention relates to novel intermediate compounds resulting from a method for forming a dihydrogen-phosphate inositol from a protected or unprotected inositol that comprises at least two vicinal trans hydroxy groups that are unprotected. This method results in each of the unprotected hydroxy groups of the inositol, which can contain from two to six unprotected hydroxy groups, being converted to a dihydrogen-phosphate group and each protected group being converted to a free hydroxy group. The method permits one to make such compounds in very few steps and in very high yields.
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- MICROBIAL OXIDATION IN SYNTHESIS: PREPARATION FROM BENZENE OF THE CELLULAR SECONDARY MESSENGER MYO-INOSITOL-1,4,5-TRISPHOSPHATE(IP3) AND RELATED DERIVATIVES
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Following microbial oxidation of benzene with Pseudomonas putida the resulting cis-1,2-dihydroxycyclohexa-3,5-diene may be converted to the cellular secondary messenger myo-inositol-1,4,5-trisphosphate(IP3) and its 6-methyl derivative.
- Ley, Steven V.,Sternfeld, Francine
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p. 5305 - 5308
(2007/10/02)
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- A VERSATILE INTERMEDIATE, D-4,5-BIS(DIBENZYL PHOSPHORYL)-MYO-INOSITOL DERIVATIVE FOR SYNTHESIS OF INOSITOL PHOSPHATES. SYNTHESIS OF 1,2-CYCLIC-4,5-, 1,4,5-, AND 2,4,5-TRISPHOSPHATE
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Practical synthesis of D-myo-inositol 1,2-cyclic-4,5-, 1,4,5-, and 2,4,5-trisphosphate was accomplished from the key synthetic intermediate, D-3,6-di-O-benzyl-4,5-di-O-(dibenzyl phosphoryl)-myo-inositol.
- Watanabe, Yutaka,Ogasawara, Tomio,Nakahira, Hiroyuki,Matsuki, Tomoko,Ozaki, Shoichiro
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p. 5259 - 5262
(2007/10/02)
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- TOTAL SYNTHESIS OF OPTICALLY ACTIVE MYO-INOSITOL 1,4,5-TRISPHOSPHATE AND MYO-INOSITOL 1,3,4,5-TETRAKISPHOSPHATE
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A convenient approach to the preparation of the title compounds illustrating selective protection, optical resolution and phosphorylation is presented.
- Dreef, C. E.,Tuinman, R. J.,Elie, C. J. J.,Marel, G. A. van der,Boom, J. H. van
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p. 395 - 397
(2007/10/02)
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- SYNTHESIS OF RACEMIC MYO-INOSITOL 1,3,4-TRIPHOSPHATE VIA A PHOSPHITE-TRIESTER APPROACH
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Phosphitylation of (+/-)- 2,4,5-tri-O-benzyl-myo-Inositol with bis(2-cyanoethyl)chlorophosphine gave, after oxidation followed by basic hydrolysis and subsequently hydrogenolysis, (+/-)-myo-Inositol 1,3,4-triphosphate.
- Dreef, C. E.,Marel, G. A. van der,Boom, J. H. van
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p. 161 - 162
(2007/10/02)
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- TOTAL SYNTHESIS OF OPTICALLY ACTIVE MYO-INOSITOL 1,4,5-TRIS(PHOSPHATE)
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Optically active myo-inositol 1,4,5-tris(phosphate) has been synthesized starting from myo-inositol.
- Ozaki, Shoichiro,Watanabe, Yutaka,Ogasawara, Tomio,Kondo, Yoshihisa,Shiotani, Naokazu,et al.
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p. 3157 - 3160
(2007/10/02)
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