An Improved Synthesis of 6-(O-Phosphorylcholine)hydroxyhexanoic Acid

Knopik, P.; Bruzik, Karol S.; Stec, Wojciech J.

doi:10.1080/00304949109458318

Cited by 7 publications

(5 citation statements)

References 4 publications

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“…The general methods of Knopik et al 36 and Das et al 37 were followed with some modifications. The potassium salt of diethyl phosphoric acid (535 mg, 2.78 mmol) and di-benzo-[18]-crown-6 (50 mg, 0.14 mmol) were added to a stirred solution of 4-(2-bromoacetyl)-3,5-dimethoxyphenyl pivalate ( 31d , 500 mg, 1.40 mmol) in CH 3 CN (10 mL).…”

Section: Synthesismentioning

confidence: 99%

p-Hydroxyphenacyl photoremovable protecting groups — Robust photochemistry despite substituent diversity

et al. 2011

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A broadly based investigation of the effects of a diverse array of substituents on the photochemical rearrangement of p-hydroxyphenacyl esters has demonstrated that common substituents such as F, MeO, CN, CO2R, CONH2, and CH3 have little effect on the rate and quantum efficiencies for the photo-Favorskii rearrangement and the release of the acid leaving group or on the lifetimes of the reactive triplet state. A decrease in the quantum yields across all substituents was observed for the release and rearrangement when the photolyses were carried out in buffered aqueous media at pHs that exceeded the ground-state pKa of the chromophore where the conjugate base is the predominant form. Otherwise, substituents have only a very modest effect on the photoreaction of these robust chromophores.

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Section: Synthesismentioning

confidence: 99%

p-Hydroxyphenacyl photoremovable protecting groups — Robust photochemistry despite substituent diversity

et al. 2011

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“…phosphocholine (2.04 GBq/mmol) and [y-32P]ATP (-185 TBq/ mmol) were from Amersham (Braunschweig, Germany). HePC was synthesized by the method of Knopik et al (1991). Silica-gel 60 high-performance t.l.c.…”

Section: Experimental Materialsmentioning

confidence: 99%

Antagonism of phorbol-ester-stimulated phosphatidylcholine biosynthesis by the phospholipid analogue hexadecylphosphocholine

Wieder

Geilen

Reutter

1993

Biochemical Journal

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The antagonization of phorbol 12-myristate 13-acetate (PMA)-stimulated phosphatidylcholine (PtdCho) biosynthesis by the phospholipid analogue hexadecylphosphocholine (HePC) in MDCK cells was investigated and compared with the corresponding influence in HeLa cells. In both cell lines, PMA-stimulated PtdCho biosynthesis was antagonized by 50 microM HePC. However, subsequent experiments provided evidence that PMA enhances PtdCho biosynthesis by at least two mechanisms: (i) by stimulation of choline uptake and (ii) by translocation of CTP:choline phosphate cytidylyltransferase to membranes. In MDCK cells, 5 nM PMA caused a 4-fold increase in [methyl-3H]choline incorporation into PtdCho, which was paralleled by an approx. 2-fold stimulation of choline uptake. These data indicate that choline uptake might play an important role in the regulation of PtdCho biosynthesis in this cell line, especially since we could not detect any significant increase in membrane-bound cytidyltransferase activity in PMA-treated MDCK cells. In contrast, enhanced PtdCho biosynthesis in HeLa cells is achieved by a 2-fold increase in particulate cytidylyltransferase activity after PMA stimulation. Translocation of cytidylyltransferase from the cytosol to membranes is therefore important in HeLa cells. Nevertheless, in both cell lines, the main target of HePC seems to be the translocation process. In MDCK cells, addition of 50 microM HePC decreases membrane-bound cytidylyltransferase activity by about 45%, compared with control cells and PMA-treated cells. In HeLa cells, PMA-induced translocation of cytidylyltransferase to membranes is totally abolished by HePC.

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Section: Methodsmentioning

confidence: 99%

“…2-(Trimethylammonio)ethyl hydrogen phosphate (compound 2) was obtained from phosphocholine chloride calcium salt tetrahydrate (1) according to the method reported in literature. 19 Next, 2 and epichlorohydrin were further used to yield 3-chloro-2-hydroxypropyl-(2-(trimethylammonio)ethyl)phosphate (3) at 90 °C for 9 h in the presence of concentrated HCl (aq). Finally, 3 was grafted onto EHL to obtain the desired production of EHLPB-x in the alkaline solution of pH = 12 at 85 °C for 5 h. The crude EHLPB-x product was further purified by acid precipitation.…”

Section: ■ Introductionmentioning

confidence: 99%

Enhancement of Recyclable pH-Responsive Lignin-Grafted Phosphobetaine on Enzymatic Hydrolysis of Lignocelluloses

Cai

et al. 2019

ACS Sustainable Chem. Eng.

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Enzymatic conversion of lignocelluloses into fermentable sugar is a key step in the production of cellulosic ethanol. In this work, enzymatic hydrolysis lignin (EHL)-grafted phosphobetaine (EHLPB) was prepared, and the phosphobetaine intermediate, 3-chloro-2-hydroxypropyl(2-(trimethylammonio)ethyl)phosphate, was synthesized from phosphocholine chloride calcium salt and epichlorohydrin. EHLPB showed a pH-sensitive response. When pH ≥ 5.0, it was completely dissolved in the buffer solution, whereas 95.5% of EHLPPB was precipitated when pH ≤ 3.0. Adding 1.2 wt % EHLPB-210 can increase the high-solid enzymatic digestibility of Eu-SPORL (sulfite pretreatment to overcome recalcitrance of eucalyptus) and CCR (corncob residue) from 33.6% and 52.6% to 71.5% and 73.6%, respectively. After the enzymatic hydrolysis of Eu-SPORL, 95% of EHLPB-210 was recovered by adjusting the slurry pH from 5 to 3. The recovered EHLPB-210 still kept the ability to enhance enzymatic hydrolysis of lignocelluloses. Adding 1.2 wt % recovered EHLPB-210 can increase the enzymatic digestibility of Eu-SPORL from 33.6% to 75.1%. Investigation of the adsorption of cellulase on lignin by sodium dodecyl sulfate–polyacylamide gel electrophoresis (SDS-PAGE) showed that EHLPB can significantly reduce the nonproductive absorption of cellulase on lignin and therefore enhance the enzymatic hydrolysis of lignocelluloses. By adding recoverable pH-responsive EHLPB, the enzymatic hydrolysis efficiency of lignocelluloses improved and the value-added utilization of enzymatic hydrolysis lignin was realized.

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An Improved Synthesis of 6-(O-Phosphorylcholine)hydroxyhexanoic Acid

Cited by 7 publications

References 4 publications

p-Hydroxyphenacyl photoremovable protecting groups — Robust photochemistry despite substituent diversity

p-Hydroxyphenacyl photoremovable protecting groups — Robust photochemistry despite substituent diversity

Antagonism of phorbol-ester-stimulated phosphatidylcholine biosynthesis by the phospholipid analogue hexadecylphosphocholine

Enhancement of Recyclable pH-Responsive Lignin-Grafted Phosphobetaine on Enzymatic Hydrolysis of Lignocelluloses

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