58706-24-4Relevant 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
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
Resolution of orthogonally protected myo-inositols with Novozym 435 providing an enantioconvergent pathway to Ac2PIM1
Lee, Alastair M. M.,Painter, Gavin F.,Compton, Benjamin J.,Larsen, David S.
, p. 10916 - 10931 (2015/01/09)
Orthogonally protected chiral myo-inositol derivatives are important intermediates for higher order myo-inositol-containing compounds. Here, the use of the immobilized enzyme Novozym 435 to efficiently catalyze the acetylation of the 5R configured enantio
Design, synthesis, and delivery properties of novel guanidine-containing molecular transporters built on dimeric inositol scaffolds
Maiti, Kaustabh K.,Jeon, Ock-Youm,Lee, Woo Sirl,Chung, Sung-Kee
, p. 762 - 775 (2007/10/03)
We have developed a novel class of synthetic molecular transporters that contain eight residues of guanidine with an inositol dimer as the scaffold. The dimers were prepared by connecting two units of myo- or scyllo-inositol via a carbonate or amide linkage, and the multiple units of the guanidine functionality were constructed on the inositol scaffold by means of peracylation with ω-aminocarboxylate derivatives of varying length. Bioassays based on confocal laser scanning microscopy and fluorescence-activated cell sorter analyses indicated that these transporters display a varying degree of membrane translocating ability, and the intracellular localization and mouse-tissue distribution studies strongly suggested that these transporters undergo substantially different mechanistic processes from those of peptide transporters reported to date. It was also shown that doxorubicin, an anticancer antibiotic, can be efficiently delivered into mouse brain by aid of this type of transporter.
Regioselective functionalizations and conformational studies of di-O-isopropylidene-myo-inositol derivatives
Chung, Sung-Kee,Ryu, Youngha
, p. 145 - 168 (2007/10/02)
(+/-)-1,2:4,5-Di-O-isopropylidene-myo-inositol (5) and (+/-)-1,2:5,6-di-O-isopropylidene-myo-inositol (6) could be regioselectively functionalized in reactions including alkylation, acylation, and silylation at HO-3 in preference to HO-6 and HO-4, respectively, under specific conditions.The presence of intramolecular hydrogen bonding was evident in IR and 1H NMR spectra, and the HO-3 group was identified as the hydrogen-bonding donor in 5 and 6.In their crystalline states, diol 5 prefers a chair conformation and diol 6 a twist boat (skew) conformation.Both compounds appear to have substantial populations of chair conformations in the gas and solution phases, on the basis of the MM-2 energy minimizations and comparisons of vicinal coupling constants observed in the 1H NMR spectra (in CDCl3 and Me2SO-d6) and calculated from the crystal and MM-2 conformations.It is suggested as an explanation for the observed selectivities that the kinetic acidity of the HO-3 group may be enhanced through its intramolecular hydrogen bonding with the cis-vicinal oxygen, or the nucleophilicity of the 3-alkoxide may be enhanced due to its interaction with the cis-vicinal oxygen in a manner similar to the through-space α-effect.
Affinity probes for ins(1,3,4,5)P4 receptors
Estevez, Virginia A.,Prestwich, Glenn D.
, p. 1623 - 1626 (2007/10/02)
A P-1-tethered derivative of Ins(1,3,4,5)P4 was synthesized and used to prepare a bioselective affinity matrix and a photoaffinity label for purification and covalent modification of IP4 receptor proteins.
The synthesis and resolution of (+/-)-1,5,6-tri-O-benzyl-myo-inositol
Desai, Trupti,Fernandez-Mayoralas, Alfonso,Gigg, Jill,Gigg, Roy,Payne, Sheila
, p. 105 - 123 (2007/10/02)
Racemic 1,5,6-O-benzyl-myo-inositol was prepared by five routes and converted into 1,5,6-tri-O-benzyl-2,3-O-isopropylidene-myo-inositol, the camphanates of which were readily separated by chromatography.The absolute configurations of the chiral derivative
Improved preparation of acetals of myo-inositol and its (+/-)-1-benzyl ether: conformational analysis of di-O-isopropylidene-myo-inositol derivatives
Pradilla, Roberto Fernandez de la,Jaramillo, Carlos,Jimenez-Barbero, Jesus,Martin-Lomas, Manuel,Penades, Soledad,Zapata, Amparo
, p. 249 - 257 (2007/10/02)
The acid-catalysed reactions of myo-inositol with 3-5 equiv. of 2-methoxypropene or 2,2-dimethoxypropane in methyl sulfoxide or N,N-dimethylformamide gave mixtures of the 1,2:4,5-, 1,2:5,6-, and 1,2:3,4-di-O-isopropylidene derivatives with little or none
THE SYNTHESIS OF (+/-)MYO-INOSITOL-1-PHOSPHONATE
Kulagowski, Janusz J.
, p. 3869 - 3872 (2007/10/02)
The synthesis of a phosphonate analogue of (+/-)-myo-inositol-1-phosphate using Horner-Emmons methodology is described.
The Allyl Group for Protection in Carbohydrate Chemistry. Part 18. Allyl and Benzyl Ethers of myo-Inositol. Intermediates for the Synthesis of myo-Inositol Triphosphates
Gigg, Jill,Gigg, Roy,Payne, Sheila,Conant, Robert
, p. 423 - 430 (2007/10/02)
Racemic 1,2:4,5-di-O-isopropylidene-myo-inositol was converted into racemic 1,2,4-tri-O-benzyl-myo-inositol, 1,2,4-tri-O-p-methoxybenzyl-myo-inositol and 2,4,5-tri-O-benzyl-myo-inositol using allyl groups for 'temporary' protection.The benzyl ethers are required as intermediates for the synthesis of the 'second messenger', inositol 1,4,5-triphosphate and its metabolite, inositol 1,3,4-triphosphate. 1,2,3,4-Tetra-O-benzyl-myo-inositol, and its two monoallyl and monoprop-1-enyl ethers, were also prepared as model compounds for phosphorylation studies of the vicinal 5,6-diol system which occurs in 1,2,4-tri-O-benzyl-myo-inositol.
