594858-37-4

Upstream product

• 170210-89-6 (+)-(1S,2R,3R,4S)-1,4-diacetoxy-2,3-dibromocyclohex-5-ene 
• 182075-57-6 1,2,3,4-tetra-O-acetylconduritol E 

Downstream Products

• 83-86-3 neo-inositol 1,2,3,4,5,6-hexakisphosphate 
• 488-54-0 neo-inositol 
• 20097-40-9 hexa-O-acetyl-neo-inositol 

Relevant academic research and scientific papers

Stereo- and regiospecificity of yeast phytases-chemical synthesis and enzymatic conversion of the substrate analogues neo- and L-chiro-inositol hexakisphosphate

Phytases are enzymes that catalyze the hydrolysis of phosphate esters in myo-inositol hexakisphosphate (phytic acid). The precise routes of enzymatic dephosphorylation by phytases of the yeast strains Saccharomyces cerevisiae and Pichia rhodanensis have been investigated up to the myo-inositol trisphosphate level, including the absolute configuration of the intermediates. Stereoselective assignment of the myo-inositol pentakisphosphates (D-myo-inositol 1,2,4,5,6-pentakisphosphate and D-myo-inositol 1,2,3,4,5-pentakisphosphate) generated was accomplished by a new method based on enantiospecific enzymatic conversion and HPLC analysis. Via conduritol B or E derivatives the total syntheses of two epimers of myo-inositol hexakisphosphate, neo-inositol hexakisphosphate and L-chiro-inositol hexakisphosphate were performed to examine the specificity of the yeast phytases with these substrate analogues. A comparison of kinetic data and the degradation pathways determined gave the first hints about the molecular recognition of inositol hexakisphosphates by the enzymes. Exploitation of the high stereo- and regiospecificity observed in the dephosphorylation of neo- and L-chiro-inositol hexakisphosphate made it possible to establish enzyme-assisted steps for the synthesis of D-neo-inositol 1,2,5,6-tetrakisphosphate, L-chiro-inositol 1,2,3,5,6-pentakisphosphate and L-chiro-inositol 1,2,3,6-tetrakisphosphate.

Stereoselective synthesis of myo-, neo-, L-chiro, D-chiro, allo-, scyllo-, and epi-inositol systems via conduritols prepared from p-benzoquinone

A practical route is described for the flexible preparation of a wide variety of inositol stereoisomers and their polyphosphates. The potential of this approach is demonstrated by the synthesis of myo-, L-chiro-, D-chiro-, epi-, scyllo-, allo-, and neo-inositol systems. Optically pure compounds in either enantiomeric form can be prepared from p-benzoquinone via enzymatic resolution of a derived conduritol B key intermediate. High-performance anion-exchange chromatography with pulsed amperometric detection permits inositol stereoisomers to be resolved and detected with high sensitivity. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.