165035-27-8Relevant academic research and scientific papers
Synthesis and iron binding studies of myo-inositol 1,2,3-trisphosphate and (±)-myo-inositol 1,2-bisphosphate, and iron binding studies of all myo-inositol tetrakisphosphates
Spiers, Ian D.,Barker, Christopher J.,Chung, Sung-Kee,Chang, Young-Tae,Freeman, Sally,Gardiner, John M.,Hirst, Peter H.,Lambert, Peter A.,Michell, Robert H.,Poyner, David R.,Schwalbe, Carl H.,Smith, Anthony W.,Solomons, Kevin R.H.
, p. 81 - 99 (1996)
The first syntheses of the natural products myo-inositol 1,2,3-trisphosphate and (±)-myoinositol 1,2-bisphosphate are described. The protected key intermediates 4,5,6-tri-O-benzoyl-myoinositol and (±)-3,4,5,6-tetra-O-benzyl-myo-inositol were phosphorylated with dibenzyl N,N-diisopropylphosphoramidite in the presence of 1H-tetrazole and subsequent oxidation of the phosphite. The crystal structures of the synthetic intermediates (±)-1-O-(tert-butyldiphenylsilyl)-2,3-O-cyclohexylidene-myo-inositol and (±)-4,5,6-tri-O-benzoyl-1-O-(tert-butyldiphenylsilyl)-2,3-O-cyclohexy lidene-myo-inositol are reported. myo-Inositol 1,2,3-trisphosphate, (±)-myo-inositol 1,2-bisphosphate, and all isomeric myo-inositol tetrakisphosphates were evaluated for their ability to alter HO· production in the iron-catalysed Haber-Weiss reaction. The results demonstrated that a 1,2,3-grouping of phosphates in myo-inositol was necessary for inhibition, also that (±)-myo-inositol 1,2-bisphosphate potentiated HO· production. myo-Inositol 1,2,3-trisphosphate resembled myo-inositol hexakisphosphate (phytic acid) in its ability to act as a siderophore by promoting iron-uptake into Pseudomonas aeruginosa.
Divergent syntheses of all possible optically active regioisomers of myo-inositol tris- and tetrakisphosphates
Chung, Sung-Kee,Kwon, Yong-Uk,Shin, Jung-Han,Chang, Young-Tae,Lee, Changgook,Shin, Boo-Gyo,Kim, Kyung-Cheol,Kim, Mahn-Joo
, p. 5626 - 5637 (2007/10/03)
Since the discovery of D-myo-inositol 1,4,5-trisphosphate, which plays a pivotal role as a second messenger in transmembrane signaling, the scope of the phosphoinositide-based signaling processes has been continually expanding. However, the clear understanding of the molecular signal transduction mechanisms including the functions of newly found IPn is still lacking. As a continuing effort to our previously reported syntheses of all possible 39 optically inactive regioisomers of myoinositol phosphates (IPn; n = 1-6), we synthesized all possible optically active regioisomers of myo-IP3 and myo-IP4 using chiral IBz3s and IBz2s, respectively. A series of procedures involving CRL-catalyzed enzymatic resolution of racemic 1,2:5,6-di-O-isopropylidene-myo-inositol and base-catalyzed benzoyl migration in tri- and dibenzoyl-isopropylidene-myo-inositol afforded eight enantiomeric pairs of IBz3 and six enantiomeric pairs of IBz2, respectively. Phosphorylation of these intermediates by the phosphitylation and oxidation procedure gave the target products.
Practical divergent synthesis of all possible regioisomers of myo-inositol trisphosphates
Chung, Sung-Kee,Chang, Young-Tae,Sohn, Kwang-Hoon
, p. 163 - 164 (2007/10/03)
The synthesis of all possible 12 regioisomers of IP3, some of which are implicated as second messengers in cellular signalling, is accomplished from myo-inositol via its tribenzoate derivatives (IBz3) as the key intermediates.
The First Synthesis and Iron Binding Studies of the Natural Product, myo-Inositol 1,2,3-Trisphosphate
Spiers, Ian D.,Freeman, Sally,Poyner, David R.,Schwalbe, Carl H.
, p. 2125 - 2128 (2007/10/02)
The natural product myo-inositol 1,2,3-trisphosphate 1 has been prepared and shown to inhibit Fe3+-catalysed hydroxyl radical formation.
