98906-30-0Relevant articles and documents
Synthesis and in vitro anticancer activity evaluation of novel bioreversible phosphate inositol derivatives
Chen, Wenbin,Deng, Zhaohui,Chen, Kuangyu,Dou, Daolei,Song, Fanbo,Li, Luyuan,Xi, Zhen
supporting information, p. 172 - 181 (2015/03/05)
The chemistry and biology of phosphorylated inositols have become intense areas of research during the last two decades due to their involvement in various cellular signaling processes. However, the metabolic instability by phosphatases or kinases and poo
Dimethyltin Dichloride Catalyzed Regioselective Alkylation of cis-1,2-Diols at Room Temperature
Saikam, Varma,Dara, Saidulu,Yadav, Mahipal,Singh, Parvinder Pal,Vishwakarma, Ram A.
, p. 11916 - 11925 (2016/01/09)
Here, we have developed a mild and general method for the regioselective installation of benzyl, allyl, para-methoxybenzyl and naphthyl groups on cis-1,2-diols. The optimized method operates at room temperature using dimethyltin dichloride as catalyst and
Kinetic resolution of a precursor for myo-inositol phosphates under continuous flow conditions
Manoel, Evelin A.,Pais, Karla C.,Flores, Marcella C.,E Miranda, Leandro Soter De M.,Coelho, Maria Alice Zarur,Simas, Alessandro B.C.,Freire, Denise M.G.,De Souza, Rodrigo Octavio M.A.
, p. 139 - 143 (2013/03/13)
In this work, we have investigated the biocatalytic continuous flow process with a packed-bed reactor for the kinetic resolution of (±)-1,3,6-tri-O- benzyl-myo-inositol ((±)-1) by alcoholysis using Novozym 435. Excellent conversions and stereselectivities were attained in short reaction time. We found that this enzymatic transformation under continuous flow in TBME with vinyl acetate (10:1 ratio with (±)-1) at 50°C, with a 3 min-residence time secured the best results (50% conversion and eep > 99%). The feasibility of a continuous operation of the Novozym 435-containing-packed-bed reactor over a longer period of time was demonstrated via a 9-cycle experiment wherein the lipase remained stable.
On the kinetic resolution of sterically hindered myo-inositol derivatives in organic media by lipases
Manoel, Evelin A.,Pais, Karla C.,Cunha, Aline G.,Coelho, Maria Alice Z.,Freire, Denise M.G.,Simas, Alessandro B.C.
, p. 47 - 52 (2012/05/20)
Sterically hindered myo-inositol derivatives were assayed against different commercial lipases. It was found that dl-1,3,6-tri-O-benzyl-myo-inositol undergoes efficient kinetic resolutions mediated by Pseudomonas sp. lipases (PS-C, PS-IM) and CaLB (Novozy
Kinetic resolution of 1,3,6-tri-O-benzyl-myo-inositol by Novozym 435: Optimization and enzyme reuse
Manoel, Evelin A.,Pais, Karla C.,Cunha, Aline G.,Simas, Alessandro B. C.,Coelho, Maria Alice Z.,Freire, Denise M. G.
, p. 1378 - 1384 (2012/11/07)
myo-Inositol derivatives bearing selectively protected hydroxyl groups are relevant precursors of high-value myo-inositols. In the present study, we applied the response surface method to the optimization of kinetic resolution of (±)-1,3,6-tri-O-benzyl-my
Synthesis and biological evaluation of phosphatidylinositol phosphate affinity probes
Conway, Stuart J.,Gardiner, James,Grove, Simon J. A.,Johns, Melloney K.,Lim, Ze-Yi,Painter, Gavin F.,Robinson, Diane E. J. E.,Schieber, Christine,Thuring, Jan W.,Wong, Leon S.-M.,Yin, Meng-Xin,Burgess, Antony W.,Catimel, Bruno,Hawkins, Phillip T.,Ktistakis, Nicholas T.,Stephens, Leonard R.,Holmes, Andrew B.
scheme or table, p. 66 - 76 (2010/04/29)
The synthesis of the complete family of phosphatidylinositol phosphate analogues (PIPs) from five key core intermediates A-E is described. These core compounds were obtained from myo-inositol orthoformate 1 via regioselective DIBAL-H and trimethylaluminium-mediated cleavages and a resolution-protection process using camphor acetals 10. Coupling of cores A-E with phosphoramidites 34 and 38, derived from the requisite protected lipid side chains, afforded the fully-protected PIPs. Removal of the remaining protecting groups was achieved via hydrogenolysis using palladium black or palladium hydroxide on carbon in the presence of sodium bicarbonate to afford the complete family of dipalmitoyl- and amino-PIP analogues 42, 45, 50, 51, 58, 59, 67, 68, 76, 77, 82, 83, 92, 93, 99 and 100. Investigations using affinity probes incorporating these compounds have identified novel proteins involved in the PI3K intracellular signalling network and have allowed a comprehensive proteomic analysis of phosphoinositide interacting proteins. The Royal Society of Chemistry 2010.
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.
General synthesis of 3-phosphorylated mj'o-inositol phospholipids and derivatives
Painter, Gavin F.,Grove, Simon J. A.,Gilbert, Lan H.,Holmes, Andrew B.,Raithby, Paul R.,Hill, Malcolm L.,Hawking, Phillip T.,Stephens, Leonard R.
, p. 923 - 935 (2007/10/03)
The D-3-phosphorylated wyo-inositol phospholipids PtdIns(3)P, PtdIns(3,4)P2, PtdIns(3,4,5)P3 and PtdIns(3,5)P2 were synthesised from /yo-inositol orthoformate 8. Key transformations included the regioselective DIBAL- and trimethylaluminium-mediated cleavages of wiyo-inositol orthoformate intermediates and a resolution-protection protocol using the camphor acetals 17. The final reductive debenzylation was effected with Pearlman's catalyst [Pd(OH)J in the presence of sodium hydrogen carbonate. The biological properties of the phospholipids were evaluated against various protein kinases (PKB and PDK-1) in which they played an important activation role.
Membrane-permeant esters of inositol polyphosphates, chemical syntheses and biological applications
Li, Wenhong,Schultz, Carsten,Llopis, Juan,Tsien, Roger Y.
, p. 12017 - 12040 (2007/10/03)
Membrane-permeant derivatives of inositol polyphosphates are useful tools for biological studies. Racemic 2,3,6-tri-O-butyryl-myo-inositol 1,4,5-trisphosphate hexakis(acetoxymethyl) ester(Bt3IP3/AM), myo-inositol 1,4,5-trisphosphate hexakis(acetoxymethyl) ester (IP3/AM), hexakis(propionyloxymethyl) ester (IP3/PM) and hexakis(butyryloxymethyl) ester (IP3/BM) were therefore synthesized. Whereas extracellular application of up to 200 μM of Bt3IP3/AM or IP3/AM to 1321N1 astrocytoma cells failed to mobilize internal calcium, IP3/PM and IP3/BM released internal calcium at concentrations as low os 20 μM and 2 μM, respectively.
