115510-58-2Relevant academic research and scientific papers
Unambiguous Total Synthesis of the Enantiomers of myo-Inositol 1,3,4-Trisphosphate: 1L-myo-Inositol 1,3,4-Trisphosphate Mobilizes Intracellular Ca2+ in Limulus Photoreceptors
Riley, Andrew M.,Payne, Richard,Potter, Barry V. L.
, p. 3918 - 3927 (2007/10/02)
Syntheses of the enantiomers of myo-inositol 1,3,4-trisphosphate are described. 1,4-Di-O-allyl-myo-inositol was regioselectively p-methoxybenzylated at the 3-position to give 1,4-di-O-allyl-3-O-(p-methoxybenzyl)-myo-inositol followed by benzylation of the remaining free hydroxyl groups to give the key intermediate 1,4-di-O-allyl-2,5,6-tri-O-benzyl-3-O-(p-methoxybenzyl)-myo-inositol.Removal of the p-methoxybenzyl and allyl groups gave 2,4,5-tri-O-benzyl-myo-inositol which was-phosphitylated with bis(benzyloxy)(diisopropylamino)phosphine to give the fully protected trisphosphite triester.Oxidation using tert-butyl hydroperoxide gave 2,5,6-tri-O-benzyl-1,3,4-tris(dibenzylphospho)-myo-inositol, and deprotection using sodium in liquid ammonia gave racemic myo-inositol 1,3,4-trisphosphate.Deprotection of the key intermediate 1,4-di-O-allyl-2,5,6-tri-O-benzyl-3-O-(p-methoxybenzyl)-myo-inositol by isomerization of allyl groups followed by mild acid hydrolysis gave 2,4,5-tri-O-benzyl-1-O-(p-methoxybenzyl)-myo-inositol, which was converted to the diastereoisomeric bis-(-)-camphanates.The diastereoisomers were separated by column chromatography and the camphanates and the p-methoxybenzyl group removed by saponification and acid hydrolysis, respectively, for each diastereoisomer to give the enantiomers of 2,4,5-tri-O-benzyl-myo-inositol.The absolute configurations of the latter were established by conversion of 1L-2,5,6-tri-O-benzyl-3-O-(p-methoxybenzyl)-myo-inositol to the known 1L-1,2,4,5,6-penta-O-benzyl-myo-inositol.Phosphorylation and deblocking gave the D- and L-enantiomers of myo-inositol 1,3,4-trisphosphate.Biological evaluation in Limulus photoreceptors showed that 1L-myo-inositol 1,3,4-trisphosphate was much more active than the D-enantiomer, producing repetitive bursts of depolarization due to mobilization of intra cellular calcium.
AN EFFICIENT ROUTE TO D-MYO-INOSITOL 1,3,4-TRIPHOSPHATE AND D-MYO-INOSITOL 1,3,4,5-TETRAKISPHOSPHATE
Gou, Da-Ming,Chen, Ching-Shih
, p. 721 - 724 (2007/10/02)
Multigram quantities of the title compounds in their enantiomerically-pure forms have been prepared by employing a chiral precursor which can be obtained via a facile enzymatic process.
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 myo-inositol polyphosphates from benzene via conduritol B derivatives
Carless, Howard A. J.,Busia, Kofi
, p. 3449 - 3452 (2007/10/02)
The four (±)-myo-inositol phosphates 1,4,5-IP3 (1), 2,4,5-IP3 (15), 1,2,4,5-IP4 (17) and 4,5-IP2 (19) have been synthesised from benzene, using the protected conduritol B (10) as the key intermediate.
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.
THE TOTAL SYNTHESIS OF myo-INOSITOL POLYPHOSPHATES
Vacca, Joseph P.,deSolms, S. Jane,Huff, Joel R.,Billington, David C.,Baker, Raymond,et al.
, p. 5679 - 5702 (2007/10/02)
Total synthesis of the individual enentiomers of myo-inositol 4-phosphate (15), myo-inositol 1,4-biphosphate (2) and myo-inositol 1,4,5-triphosphate (1), together with syntheses of racemic myo-inositol 1,3,4-triphosphate (4) and myo-inositol 2,4,5-triphos
FLUORINATED ANALOGS AND TRITIATED ENANTIOMERS OF INOSITOL (1,3,4)-TRISPHOSPHATE
Boehm, Marcus F.,Prestwich, Glenn D.
, p. 5217 - 5220 (2007/10/02)
The total syntheses of 2-fluoro- and 2,2-difluoro-2-deoxy analogs of DL-myo-Ins(1,3,4)P3 are described.Resolution of a key intermediate followed by borotritide reduction and phosphorylation provided both D- and L--Ins(1,3,4)P3 enantiomers with spe
Synthesis of Optically Active myo-Inositol 1,3,4-Triphosphate
Ozaki, Shoichiro,Kohno, Masayasu,Nakahira, Hiroyuki,Bunya, Motonobu,Watanabe, Yutaka
, p. 77 - 80 (2007/10/02)
Synthesis of optically active myo-inositol 1,3,4-triphosphate has been accomplished.Efficiency of a chiral HPLC column for optical resolution of myo-inositols is shown.
