111408-68-5Relevant academic research and scientific papers
Syntheses of D- and L-myo-inositol 1,2,4,5-tetrakisphosphate and stereoselectivity of the I(1,4,5)P3 receptor binding.
Chung,Shin,Chang,Suh,Kim
, p. 659 - 662 (1998)
D- and L-myo-Inositol 1,2,4,5-tetrakisphosphate [D- & L-I(1,2,4,5)P4], which are analogues of D-myo-Inositol 1,4,5-trisphosphate [D-I(1,4,5)P3], a calcium mobilizing second messenger, were synthesized via resolution of the camphanate ester of a myo-inositol derivative, and the binding affinities to I(1,4,5)P3 receptor were measured.
Design and synthesis of lipid-coupled inositol 1,2,3,4,5,6-hexakisphosphate derivatives exhibiting high-affinity binding for the HIV-1 MA domain
Tateishi, Hiroshi,Anraku, Kensaku,Koga, Ryoko,Okamoto, Yoshinari,Fujita, Mikako,Otsuka, Masami
, p. 5006 - 5022 (2014/07/07)
The precursor of Gag protein (Pr55Gag) of human immunodeficiency virus, the principal structural component required for virus assembly, is known to bind d-myo-phosphatidylinositol 4,5-bisphosphate (PIP2). The N-terminus of Pr55G
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.
experimental part, 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
Tetrakisphosphates and Bispyrophosphates of myo-Inositol Derivatives as Allosteric Effectors of Human Hemoglobin: Synthesis, Molecular Recognition, and Oxygen Release
Koumbis, Alexandros E.,Duarte, Carolina D.,Nicolau, Claude,Lehn, Jean-Marie
, p. 169 - 180 (2013/01/09)
Various 2,5- and 1,4-substituted and unsubstituted myo-inositol tetrakisphosphates and bispyrophosphates were prepared following a general synthetic pathway. All final compounds were tested for their capability to induce oxygen release from human hemoglob
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
Regiospecific phosphohydrolases from Dictyostelium as tools for the chemoenzymatic synthesis of the enantiomers D-myo-inositol 1,2,4-trisphosphate and D-myo-inositol 2,3,6-trisphosphate: Non-physiological, potential analogues of biologically active D-myo-
Adelt, Stephan,Plettenburg, Oliver,Dallmann, Guido,Ritter, Frank P.,Shears, Stephen B.,Altenbach, Hans-Josef,Vogel, Guenter
, p. 2705 - 2708 (2007/10/03)
A new de novo synthesis of the enantiomeric pair D-myo-inositol 1,2,4-trisphosphate and D-myo-inositol 2,3,6-trisphosphate is described. Starting from enantiopure dibromocyclohexenediol, several C2 symmetrical building blocks were synthesized w
Synthesis of 2-deoxy-2-fluoro-phosphatidylinositol-4,5-bisphosphate and analoglies: Probes and modulators of the mammalian PI-PLCs
Aneja, Sarla G.,Ivanova, Pavlina T.,Aneja, Rajindra
, p. 1061 - 1064 (2007/10/03)
An approach to synthesis of 2-modified phosphatidylinositol-4,5- bisphosphates, which are substrate analogues useful as probes and modulators of the PI-PLC enzyme family, is described and illustrated for the dibutyl-2- deoxy-2-fluoro analogue, a probe designed for delineating substrate and PI- PLC interactions by X-ray crystallography.
Synthesis of the enantiomers of myo-inositol 1,2,4,5-tetrakisphosphate, a regioisomer of myo-inositol 1,3,4,5-tetrakisphosphate
Mills, Stephen J.,Potter, Barry V. L.
, p. 1279 - 1286 (2007/10/03)
Routes for the synthesis of racemic myo-inositol 1,2,4,5-tetrakisphosphate DL-Ins(1,2,4,5)P4 5ab and the chiral antipodes D- and L-myo-inositol 1,2,4,5-tetrakisphosphate 5a and 5b, respectively, are described. For the synthesis of racemate 5ab, 3,6-di-O-benzoyl-1,2:4,5-di-O-isopropylidene-myo-inositol 7ab is prepared in two steps from myo-inositol. The ketals are hydrolysed under acidic conditions to give DL-1,4-di-O-benzoyl-myo-inositol 8ab. Phosphitylation of compounds 8ab using chloro(diethoxy)-phosphine in the presence of base, followed by oxidation and a three-step deprotection strategy, gives DL-Ins(1,2,4,5)P4 5ab. The chiral tetrakisphosphates 5a and 5b are synthesized using a different route. The 4,5-isopropylidene group of DL-3,6-di-O-benzyl-1,2:4,5-di-O-isopropylidene-myo-inositol 13ab are selectively removed under mild acidic conditions to give diol 14ab. p-Methoxybenzylation at the 4,5-positions followed by acid hydrolysis of the cis-isopropylidene ketal affords cis-diol 16ab. Selective coupling of (S)-(+)-O-acetylmandelic acid with diol 16ab at the equatorial hydroxy group provides two diastereoisomers 18 and 19, which are separated by chromatography. Basic hydrolysis of the individual diastereoisomers provides the enantiomers 16a and 16b. Acidic hydrolysis gives D- and L-3,6-di-O-benzyl-myo-inositol 20a and 20b, respectively. Phosphitylation and oxidation of tetraols 20a and 20b gives the fully blocked derivatives, which are deprotected to give tetrakisphosphates 5a and 5b, respectively. The absolute configuration of compound 20a is established by a chemical method. DL-1,2:4,5-Di-O-isopropylidene-myo-inositol 12ab is coupled to (S)-(+)-O-acetylmandelic acid to give a mixture of bis-esters 26 and 27 and crystallisation of the mixture of diastereoisomers affords pure isomer 27. Basic hydrolysis gives the pure enantiomer 12a (for which the absolute configuration is known) and benzylation followed by acid hydrolysis gives tetraol 20a with the same physical properties as compound 20a prepared by a different route described previously. D-Ins(1,2,4,5)P4 5a is a potent mobiliser of intracellular Ca2+ ions in permeabilised platelets, while L-Ins(1,2,4,5)P4 5b is inactive.
Synthesis and Some Properties of D-myo-Inositol 1,4,5-Tris(dihydrogen phosphate)
Ozaki, Shoichiro,Kondo, Yoshihisa,Shiotani, Naokazu,Ogasawara, Tomio,Watanabe, Yutaka
, p. 729 - 738 (2007/10/02)
Optically active myo-inositol 1,4,5-tris(dihydrogen phosphate) 1, which has now been recognized as a second messenger in a new intracellular signal transduction system, has been prepared starting from myo-inositol.The key step, phosphorylation of an adequately protected polyhydroxy derivative, was accomplished by three methods, among which a phosphoramidite method using a new phosphitylating agent, o-xylylene N,N-diethylphosphoramidite, gave the triphosphoric ester in quantitative yield.Optical resolution was effectively realized by derivatization into diastereoisomeric l-menthoxyacetic esters.NMR spectra and optical rotation are shown to depend on the pH of an aqueous solution of compound 1.
TOTAL SYNTHESIS OF chiro-INOSITOL 2,3,5-TRISPHOSPHATE: A myo-INOSITOL 1,4,5-TRISPHOSPHATE ANALOGUE FROM BENZENE VIA PHOTO-OXIDATION
Carless, Howard A. J.,Busia, Kofi
, p. 1617 - 1620 (2007/10/02)
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.
