115184-71-9Relevant academic research and scientific papers
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
, 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.
Direct selective and controlled protection of multiple hydroxyl groups in polyols via iterative regeneration of stannylene acetals
Simas, Alessandro B.C.,da Silva, Angelo A.T.,dos Santos Filho, Tarcizio J.,Barroso, Pedro T.W.
supporting information; experimental part, p. 2744 - 2746 (2009/09/25)
A direct selective protection (O-benzylation) of two or more hydroxyl groups in polyols displaying diverse structural patterns was made possible by the establishment of conditions that enable an efficient turnover for the Bu2Sn group, initially
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
A more convenient and general procedure for O-monobenzylation of diols via Stannylenes: A critical reevaluation of the Bu2SnO method
Simas, Alessandro B. C.,Pais, Karla C.,Da Silva, Angelo A. T.
, p. 5426 - 5428 (2007/10/03)
A more consistent, straightforward, and economical protocol for generation of stannylene species and their reaction with BnBr leading to products of O-monobenzylation of diols has been set. It has shown to be specially indicated for substrates bearing vicinal trans 1,2-diol moieties on cyclohexane backbones, which are more resistant to these transformations. Such protocol has been successfully applied to myo-inositol derivatives and acyclic diols.
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.
