92216-45-0Relevant articles and documents
Incorporation of a fluorous diazirine group into phosphatidylinositol 4,5-bisphosphate to illustrate its interaction with ADP-ribosylation factor 1
Huang, Weigang,Sun, Wei,Song, Zhiquan,Yu, Yanbao,Chen, Xian,Zhang, Qisheng
body text, p. 5197 - 5201 (2012/08/08)
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.
FLUOROGENIC SENSORS FOR PHOSPHOLIPASE C ISOZYMES
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Page/Page column 28; 34, (2012/01/05)
The present invention provides fluorogenic substrates and methods of use in detecting and analyzing phospholipase C isozyme (PLC) activity.
Synthesis of unsaturated phosphatidylinositol 4,5-bisphosphate and analogues
Panchal, Nitesh,Gaffney, Piers R. J.
experimental part, p. 4832 - 4841 (2010/02/16)
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
Flexible stereo- and regioselective synthesis of myo-inositol phosphates (part 1): Via symmetrical conduritol B derivatives
Podeschwa, Michael A. L.,Plettenburg, Oliver,Altenbach, Hans-Josef
, p. 3101 - 3115 (2007/10/03)
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
Synthesis of D- and L-myo-inositol 2,4,5-trisphosphate and trisphosphorothioate: structural analogues of D-myo-inositol 1,4,5-trisphosphate.
Mills, Stephen J,Liu, Changsheng,Potter, Barry V L
, p. 1795 - 1801 (2007/10/03)
The preparation of D- and L-myo-inositol 2,4,5-trisphosphate is described, together with the phosphorothioate counterparts. The known chiral diols D- and L-1,4-di-O-benzyl-5,6-bis-O-p-methoxybenzyl-myo-inositol were regioselectively protected at the 3-position using a benzyl group via a 2,3-O-stannylene acetal. Removal of the p-methoxybenzyl groups of each enantiomer gave D- and L-1,3,6-tri-O-benzyl-myo-inositol. Phosphitylation with bis(benzyloxy)diisoproplyaminophosphine and 1H-tetrazole gave the trisphosphite intermediate for each enantiomer. Oxidation with 3-chloroperoxybenzoic acid gave the fully protected D- and L-myo-inositol 2,4,5-trisphosphates. Sulphoxidation of the D- and L-2,4,5-trisphosphite intermediates gave the fully protected D- and L-myo-inositol 2,4,5-trisphosphorothioate compounds. The fully protected trisphosphates were deblocked using hydrogenolysis and the phosphorothioates were deprotected using sodium in liquid ammonia. The individual compounds were then purified using ion exchange chromatography to afford pure D- and L-myo-inositol 2,4,5-trisphosphates together with the corresponding phosphorothioates.
Divergent syntheses of all possible optically active regioisomers of myo-inositol tris- and tetrakisphosphates
Chung, Sung-Kee,Kwon, Yong-Uk,Shin, Jung-Han,Chang, Young-Tae,Lee, Changgook,Shin, Boo-Gyo,Kim, Kyung-Cheol,Kim, Mahn-Joo
, p. 5626 - 5637 (2007/10/03)
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.
Novel synthesis of enantiomerically pure natural inositols and their diastereoisomers
Takahashi,Kittaka,Ikegami
, p. 2705 - 2716 (2007/10/03)
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.
Rapid and practical synthesis of D-myo-inositol 1,4,5-trisphosphate
Garrett, Shane W.,Liu, Changsheng,Riley, Andrew M.,Potter, Barry V. L.
, p. 1367 - 1368 (2007/10/03)
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.
Novel synthesis of enantiomerically pure natural inositols and their diastereomers
Takahashi, Hideyo,Kittaka, Hisae,Ikegami, Shiro
, p. 9707 - 9710 (2007/10/03)
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).
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)
Leung, Lawrence W.,Bittman, Robert
, p. 171 - 179 (2007/10/03)
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.
