28841-62-5

Usage

InChI:InChI=1/C6H15O15P3/c7-1-2(8)4(19-22(10,11)12)6(21-24(16,17)18)5(3(1)9)20-23(13,14)15/h1-9H,(H2,10,11,12)(H2,13,14,15)(H2,16,17,18)/t1?,2-,3+,4-,5-,6?/m1/s1

Upstream product

• 26326-85-2 Ins(1,2,3,4,6)P5 
• 454199-95-2 L-1,2,6-tri-O-benzoyl-3,4-O-isopropylidene-myo-inositol 
• 454200-06-7 L-1,6-di-O-benzoyl-3,4-O-isopropylidene-myo-inositol 
• 455268-36-7 L-1,2,6-tri-O-benzoyl-myo-inositol 
• 165883-87-4 L-1,6-di-O-benzoyl-myo-inositol 
• 142630-99-7 1D-3,4,5-O-tribenzoyl-myo-inositol 
• 26326-86-3 Ins(1,2,3,4,5)P₅ 
• 83-86-3 phytic acid 

Downstream Products

• 166660-37-3 1D-3,4,5-tri-O-propanoyl-myo-inositol-1,2,6-tris(dihydrogenphosphate) 
• 194786-37-3 6-O-(1'-ethoxyethyl)-1,2-O-isopropylidene-4,5,6-tri-O-(N-phenylcarbamoyl)-myo-inositol 
• 194786-36-2 (+)-D-1,2-O-isopropylidene-3,4,5-tri-O-(N-phenylcarbamoyl)-myo-inositol 
• 194786-39-5 (3aR,4R,5S,6S,7R,7aS)-4,5,6-Tris-benzyloxy-7-(1-ethoxy-ethoxy)-2,2-dimethyl-hexahydro-benzo[1,3]dioxole 
• 172219-04-4 (+)-D-3,4,5-tri-O-phenylcarbamoyl myo-inositol 
• 131233-69-7 3,4,5-tri-O-benzyl-D-myo-inositol 
• 166660-36-2 (+)-D-3,4,5-tri-O-(N-phenylcarbamoyl)-myo-inositol-1,2,3-tris(phosphate) 

Relevant academic research and scientific papers

Pathway of dephosphorylation of myo-inositol hexakisphosphate by phytases of legume seeds

Using a combination of high-performance ion chromatography analysis and kinetic studies, the pathway of dephosphorylation of myo-inositol hexakisphosphate by the phytases purified from faba bean and lupine seeds, respectively, was established. The data demonstrate that the legume seed phytases under investigation dephosphorylate myo-inositol hexakisphosphate in a stereospecific way. The phytase from faba bean seeds and the phytase LP2 from lupine seeds degrade phytate by sequential removal of phosphate groups via D-Ins(1,2,3,5,6)P5, D-Ins(1,2,5,6)P4, D-Ins(1,2,6)P3, and D-Ins(1,2)P2 to finally Ins(2)P, whereas the phytases LP11 and LP12 from lupine seeds generate the final degradation product Ins(2)P via D-Ins(1,2,4,5,6)P5, D-Ins(1,2,5,6)P4, D-Ins(1,2,6)P3, and D-Ins(1,2)P2.

Divergent syntheses of all possible optically active regioisomers of myo-inositol tris- and tetrakisphosphates

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.

Synthesis of optically active myo-inositol derivatives starting from phytic acid

Phytic acid treated with Baker's yeast gave D-myo-inositol-1,2,6-tris(phosphate) (α-trinositol) which was transformed into (+)-D-1,2-O-isopropylidene-myo-inositol and (-)-D-4,5-tri- O-benzyl-myo-inositol, two key intermediates in the synthesis of optically active myo-inositol derivatives and related compounds.

Enzyme assisted synthesis of D-myo-inositol-1,2,6-trisphosphate

The title compound is prepared in enantiomerically pure form via a facile enzyme assisted route. Essential for the success of the described method were a) the highly enantioselective esterification of 4,6-O-dibenzoyl-myo-inositol 2, b) the selective acylation of the axial hydroxyl function in 3 and c) the selective, base catalysed methanolysis of one benzoate group in 5. The obtained, selectively protected 1,2,6-triol 6 was converted into the title compound 7 by phosphorylation using N,N-dimethyl dibenzyl phosphoamidite followed by deprotection.