144068-89-3Relevant academic research and scientific papers
Relative reactivity of hydroxyl groups in inositol derivatives: role of metal ion chelation
Devaraj, Subramanian,Jagdhane, Rajendra C.,Shashidhar, Mysore S.
experimental part, p. 1159 - 1166 (2009/10/04)
O-Alkylation of myo-inositol derivatives containing more than one hydroxyl group via their alkali metal alkoxides (sodium or lithium) preferentially occurs at a hydroxyl group having a vicinal cis-oxygen atom. In general the observed selectivity is relatively higher for lithium alkoxides than for the corresponding sodium alkoxide. The observed regioselectivity is also dependent on other factors such as the solvent and reaction temperature. A perusal of the results presented in this article as well as those available in the literature suggests that chelation of metal ions by inositol derivatives plays a significant role in the observed regioselectivity. Steric factors associated with the axial or equatorial disposition of the reacting hydroxyl groups do not contribute much to the outcome of these O-alkylation reactions. These results could serve as guidelines in planning synthetic strategies involving other carbohydrates and their derivatives.
New fluorescent probes reveal that flippase-mediated flip-flop of phosphatidylinositol across the endoplasmic reticulum membrane does not depend on the stereochemistry of the lipid
Vishwakarma, Ram A.,Vehring, Stefanie,Mehta, Anuradha,Sinha, Archana,Pomorski, Thomas,Hermann, Andreas,Menon, Anant K.
, p. 1275 - 1283 (2007/10/03)
Glycerophospholipid flip-flop across biogenic membranes such as the endoplasmic reticulum (ER) is a fundamental feature of membrane biogenesis. Flip-flop requires the activity of specific membrane proteins called flippases. These proteins have yet to be i
Antagonists of myo-inositol 3,4,5,6-tetrakisphosphate allow repeated epithelial chloride secretion
Rudolf, Marco T.,Dinkel, Carlo,Traynor-Kaplan, Alexis E.,Schultz, Carsten
, p. 3315 - 3329 (2007/10/03)
Cystic fibrosis (CF) patients suffer from a defect in hydration of mucosal membranes due to mutations in the cystic fibrosis transmembrane regulator (CFTR), an apical chloride channel in mucosal epithelia. Disease expression in CF knockout mice is organ s
Syntheses of penta-O-benzyl-myo-inositols, O-β-L-arabinosyl-(1 → 2)sn-myo-inositol, O-α-D-galactosyl-(1 → 3)-sn-myo-inositol, and O-α-D-galactosyl-(1 → 6)-O-α-D-galactosyl-(1 → 3)-sn-myo-inositol
Koto,Hirooka,Yoshida,Takenaka,Nagamitsu,Sakurai,Zen,Yago,Tomonaga
, p. 2521 - 2529 (2007/10/03)
Two-step conversions of myo-inositol into (±)-2,3,4,5,6- and 1,3,4,5,6-penta-O-benzyl-myo-inositols are described. Starting from these monohydroxy derivatives of myo-inositol, O-β-L-arabinopyranosyl-(1→2)-sn-myo-inositol from Japanese green tea, Camellia sinensis, and O-α-D-galactopyranosyl-(1→3)-sn-myo-inositol (galactinol) as well as its homolog, O-α-D-galactopyranosyl-(1→6(II))-galactinol, were synthesized by way of the in situ activating glycosylation procedure.
Inositol polyphosphates and methods of using same
-
, (2008/06/13)
The present invention provides compositions that are cell permeable antagonists of inositol polyphosphates. In addition, the invention provides methods for enhancing chloride ion secretion from a cell by contacting the cells with cell permeable antagonists of inositol polyphosphates. The invention also provides methods for enhancing chloride ion secretion in an individual by administering cell permeable antagonists of inositol polyphosphates to the individual. The invention additionally provides methods for alleviating a sign or symptom associated with cystic fibrosis in an individual by administering a cell permeable antagonist of inositol polyphosphates to the individual. The invention also provides compositions that are cell permeable agonists of inositol polyphosphates. In addition, the invention provides methods for decreasing chloride ion secretion from a cell by contacting the cell with cell permeable agonists of inositol polyphosphates. The invention also provides methods for decreasing chloride ion secretion in an individual by administering cell permeable agonists of inositol polyphosphates to the individual. The invention additionally provides methods for alleviating a sign or symptom associated with secretory diarrhea in an individual by administering cell permeable agonists of inositol polyphosphates to the individual.
The absolute configuration of (+)-1,2,4,5,6-penta-O-benzyl-myo-inositol
Aneja,Aneja,Pathak,Ivanova
, p. 6061 - 6062 (2007/10/02)
The absolute configuration of (+)-1,2,4,5,6-penta-O-benzyl-myo-inositol is correlated with 1D-1,4,5,6-tetra-O-benzyl-myo-inositol and thus confirmed as 1D-1,2,4,5,6-penta-O-benzyl-myo-inositol.
Synthesis of phosphatidyl-2-O-alkylinositols as potential inhibitors for PI specific PLC
Garigapati,Roberts
, p. 5579 - 5582 (2007/10/02)
(±)-Racemic phosphatidyl-2-O-methylinositol and phosphatidyl-2-O-heptylinositol were synthesized and tested as mechanism-based inhibitors of bacterial PI-PLC activity.
AN APPROACH TOWARD THE SYNTHESIS OF RACEMIC MYO-INOSITOL 1-( 3,4-DI-PALMITOYLOXYBUTYL)-SULFONATE
Elle, C. J. J.,Dreef, C. E.,Brounts, D. M.,Marel, G. A. van der,Boom, J. H. van
, p. 92 - 94 (2007/10/02)
Substitution of the triflate function in 1,2-isopropylidene-sn-glycerol 3-trifluoromethanesulfonate by the α-lithio-anion of 2,3,4,5,6-penta-O-benzyl-myo-inositol 1-methanesulfonate afforded, after acid hydrolysis of the acetonide function, followed by pa
Synthesis of D- and L-myo-Inositol 1-phosphorothioate, Substrates for Inositol Monophosphatase
Baker, Graham R.,Billington, David C.,Gani, David
, p. 3895 - 3908 (2007/10/02)
The D- and L- enantiomers of myo-inositol 1-phosphorothioate have been synthesized from 2,3,4,5,6-pentakis-O-benzyl myo-inositol in 6 steps, both compounds are substrates for inositol monophosphatase.D-glucopyranose 6-phosphorothioate did not serve as a s
The synthesis of DL-1-(hexadecanoyloxy)methyl- and 1-O-hexadecanoyl-inositols as potential inhibitors of phospholipase C
James,Massy,Wyss
, p. 1037 - 1057 (2007/10/02)
The synthesis of racemic analogues of phosphatidylinositol (PI) and phosphatidylinositol 4,5-bisphosphate (PIP2) starting from myo-inositol is described. Inositol derivatives with and without homologation at C(1) and with and without ionic grou
