A synthesis of (±)myo-inositol 1-phosphate

Kiely, Donald E.; Abruscato, Gerald J.; Baburao, V.

doi:10.1016/s0008-6215(00)82905-5

Cited by 25 publications

(7 citation statements)

References 12 publications

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“…The composition of each substrate (i.e., the inositol/phosphate content) was determined by fastatom-bombardment mass spectrometry (Sherman et al, 1986a) as well as by high-voltage paper electrophoresis (Seiffert & Agranoff, 1965). L-Ins(I)P was obtained from Elastin Products Co., St. Louis, MO, U.S.A. DL-Ins(l)P was synthesized (Kiely et al, 1974).…”

Section: Vol 242mentioning

confidence: 99%

Evidence that inositol 1-phosphate in brain of lithium-treated rats results mainly from phosphatidylinositol metabolism

Ackermann¹,

Gish²,

Honchar³

et al. 1987

Biochemical Journal

120

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In cerebral cortex of rats treated with increasing doses of LiCl, the relative concentrations of Ins(1)P, Ins(4)P and Ins(5)P (when InsP is a myo-inositol phosphate) are approx. 10:1:0.2 at all doses. In rats treated with LiCl followed by increasing doses of pilocarpine a similar relationship occurs. myo-Inositol-1-phosphatase (InsP1ase) from bovine brain hydrolyses Ins(1)P, Ins(4)P and Ins(5)P at comparable rates, and these substrates have similar Km values. The hydrolysis of Ins(4)P is inhibited by Li+ to a greater degree than is hydrolysis of Ins(1)P and Ins(5)P. D-Ins(1,4,5)P3 and D-Ins(1,4)P2 are neither substrates nor inhibitors of InsP1ase. A dialysed high-speed supernatant of rat brain showed a greater rate of hydrolysis of Ins(1)P than of D-Ins(1,4)P2 and a lower sensitivity of the bisphosphate hydrolysis to LiCl, as compared with the monophosphate. That enzyme preparation produced Ins(4)P at a greater rate than Ins(1)P when D-Ins(1,4)P2 was the substrate. The amount of D-Ins(3)P [i.e. L-Ins(1)P, possibly from D-Ins(1,3,4)P3] is only 11% of that of D-Ins(1)P on stimulation with pilocarpine in the presence of Li+. DL-Ins(1,4)P2 was hydrolysed by InsP1ase to the extent of about 50%; both Ins(4)P and Ins(1)P are products, the former being produced more rapidly than the latter; apparently L-Ins(1,4)P2 is a substrate for InsP1ase. Li+, but not Ins(2)P, inhibited the hydrolysis of L-Ins(1,4)P2. The following were neither substrates nor inhibitors of InsP1ase; Ins(1,6)P2, Ins(1,2)P2, Ins(1,2,5,6)P4, Ins(1,2,4,5,6)P5, Ins(1,3,4,5,6)P5 and phytic acid. myo-Inositol 1,2-cyclic phosphate was neither substrate nor inhibitor of InsP1ase. We conclude that the 10-fold greater tissue contents of Ins(1)P relative to Ins(4)P in both stimulated and non-stimulated rat brain in vivo are the consequence of a much larger amount of PtdIns metabolism than polyphosphoinositide metabolism under these conditions.

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Section: Vol 242mentioning

confidence: 99%

Evidence that inositol 1-phosphate in brain of lithium-treated rats results mainly from phosphatidylinositol metabolism

Ackermann¹,

Gish²,

Honchar³

et al. 1987

Biochemical Journal

120

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“…As an InsP4 model compound, racemic 1,4,5,6-InsP4 (18) was synthesized over four steps (Scheme 2). In brief, ketalization of myo-inositol (1) furnished tetra-ol 15 in accordance with the literature [28]. Phosphorylation of tetra-ol 15 with AB-P-amidite S1 (see Supplementary Materials) afforded the AB-protected-InsP4 derivative 16.…”

Section: Chemical Synthesis Of Insp Model Compoundsmentioning

confidence: 54%

“…Racemic 1,4,5-InsP 3 (14) was synthesized over eight steps (Scheme 1). Starting from myo-inositol (1) different protecting groups were introduced to obtain the protected inositol 9 in accordance with the literature [28][29][30][31]. Subsequent protection of the 4-/6-position with an MEM group followed by selective cleavage of the silyl protecting groups gave triol 11.…”

Section: Chemical Synthesis Of Insp Model Compoundsmentioning

confidence: 99%

“…The pyrophosphate was generated by phosphorylation with Bn-phosphoramidite S4 (see Supplementary Materials) [35]. 5-PP-InsP 1 (28) was obtained by cleaving the remaining protecting groups under hydrogenative conditions.…”

Section: Chemical Synthesis Of Insp Model Compoundsmentioning

confidence: 99%

“…The shifts are strongly dependent on the pH value and the counterions [36]. Another novel compound that was synthesized in the context of this study is 5-PP-1/3-InsP1 (28). The molecule was made starting from myo-inositol (1) in nine steps (Scheme 4).…”

Section: Enantiomer Assignment By 31 P-nmr Using a Chiral Solvating A...mentioning

confidence: 99%

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Assigning the Absolute Configuration of Inositol Poly- and Pyrophosphates by NMR Using a Single Chiral Solvating Agent

Ritter,

Jork,

Unmüßig

et al. 2023

Biomolecules

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Inositol phosphates constitute a family of highly charged messenger molecules that play diverse roles in cellular processes. The various phosphorylation patterns they exhibit give rise to a vast array of different compounds. To fully comprehend the biological interconnections, the precise molecular identification of each compound is crucial. Since the myo-inositol scaffold possesses an internal mirror plane, enantiomeric pairs can be formed. Most commonly employed methods for analyzing InsPs have been geared towards resolving regioisomers, but they have not been capable of resolving enantiomers. In this study, we present a general approach for enantiomer assignment using NMR measurements. To achieve this goal, we used 31P-NMR in the presence of L-arginine amide as a chiral solvating agent, which enables the differentiation of enantiomers. Using chemically synthesized standard compounds allows for an unambiguous assignment of the enantiomers. This method was applied to highly phosphorylated inositol pyrophosphates, as well as to lowly phosphorylated inositol phosphates and bisphosphonate analogs. Our method will facilitate the assignment of biologically relevant isomers when isolating naturally occurring compounds from biological specimens.

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The synthesis of DL‐1‐(hexadecanoyloxy)methyl‐ and 1‐O‐hexadecanoyl‐inositols as potential inhibitors of phospholipase C

James

Massy

Wyss

1990

Helvetica Chimica Acta

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The synthesis of racemic analogues of phosphatidylinositol (PI) and phosphatidylinositol4,S-bisphosphate (PIP,) starting from myo-inositol is described. Inositol derivatives with and without homologation at C( 1) and with and without ionic groups (phosphate or sulfate) at C(4) and C(5) were prepared as well as homologated derivatives with deoxy composition at C(2) and/or C(6). In all these compounds, palmitate ester groups were introduced in place of the diacylglyceryl group of PI or PIP2.

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A synthesis of (±)myo-inositol 1-phosphate

Cited by 25 publications

References 12 publications

Evidence that inositol 1-phosphate in brain of lithium-treated rats results mainly from phosphatidylinositol metabolism

Evidence that inositol 1-phosphate in brain of lithium-treated rats results mainly from phosphatidylinositol metabolism

Assigning the Absolute Configuration of Inositol Poly- and Pyrophosphates by NMR Using a Single Chiral Solvating Agent

The synthesis of DL‐1‐(hexadecanoyloxy)methyl‐ and 1‐O‐hexadecanoyl‐inositols as potential inhibitors of phospholipase C

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