41158-67-2

Basic information

• Product Name: myo-inositol-1,2-cyclic phosphate
• Synonyms: myo-inositol-1,2-cyclic phosphate
• CAS NO: 41158-67-2
• Molecular Weight: 242.122
• Mol File: 41158-67-2.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: myo-inositol-1,2-cyclic phosphate(CAS DataBase Reference)
• NIST Chemistry Reference: myo-inositol-1,2-cyclic phosphate(41158-67-2)
• EPA Substance Registry System: myo-inositol-1,2-cyclic phosphate(41158-67-2)

Safety Data

• Hazardous Substances Data: 41158-67-2(Hazardous Substances Data)

Upstream product

• 573-35-3 myo-Inositol 2-phosphate 
• 143678-64-2 p-nitrophenyl 1-inositol phosphate 
• 2645-22-9 dipyridin-4-yl disulfide 
• 87-89-8 D-myo-inositol 
• 75194-94-4 3,3,7,7-tetramethyl-2,8-dioxa-5-aza-1λ³-phosphabicyclo(3,3,0)octane 

Downstream Products

• 129830-95-1 sn-glycero-3-phospho-(1'-myo-inositol) 

Relevant articles and documents

Synthesis and Kinetic Evaluation of Inhibitors of the Phosphatidylinositol-Specific Phospholipase C from Bacillus cereus

Substrate analogues of phosphatidylinositol (1) were synthesized and evaluated as potential inhibitors of the bacterial phosphatidylinositol-specific phospholipase C (PI-PLC) from Bacillus cereus.The chiral analogues of the water-soluble phospholipid substrate 5 were designed to probe the effects of varying the inositol C-2 hydroxyl group, which generally believed to serve as the nucleophile in the first step of the hydrolysis of phosphatidylinositols by PI-PLC.In the analogues 6-9, the C-2 hydroxyl group on the inositol ring of the phosphatidylinositol derivatives was rationally altered in several ways.Inversion of the stereochemistry at C-2 of the inositol ring led to the scyllo derivative 6.The inositol C-2 hydroxy group was replaced with inversion by a fluorine to produce the scyllo-fluoro inositol 7 and with a hydrogen atom to furnish the 2-deoxy compound 8.The C-2 hydroxyl group was O-methylated to prepare the methoxy derivative 9.The natural inositol configuration at C-2 was retained in the nonhydrolyzable phosphorodithioate analogue 10.The inhibition of PI-PLC by each of these analogues was then analyzed in a continuous assay using D-myo-inositol 1-(4-nitrophenyl phosphate) (25) as a chromogenic substrate.The kinetic parameters for each of these phosphatidylinositol derivatives were determined, and each was found to be a competitive inhibitor with Ki's as follows: 6, 0.2 mM; 10, 0.6 mM; 8, 2.6 mM; 9, 6.6 mM; and 7, 8.8 mM.This study further establishes that the hydrolysis of phosphatidylinositol analogues by bacterial PI-PLC requires not only the presence of a C-2 hydroxyl group on the inositol ring, but the stereochemistry at this position must also correspond to the natural myo-configuration.For future inhibitor design, it is perhaps noteworthy that the best inhibitors 6 and 10 each possess a hydroxyl group at the 2-position.Several of the inhibitors identified in this study are now being used to obtain crystallographic information for an enzyme-inhibitor complex to gain further insights regarding the mechanism of hydrolysis of phosphatidylinositides by this PI-PLC.

PHOSPHORANYLATION OF MYO-INOSITOL: A NEW ROUTE FOR A SIMULTANEOUS SYNTHESIS OF SEVERAL MYO-INOSITOL PHOSPHATES

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