ホスホリルコリン

化学的特性White crystal or crystalline powder, slightly fishy odor. Melting point 200～205°C(sealed tube). Has deliquescence. Insoluble in general organic solvents such as benzene, chloroform and ether, slightly soluble in ethanol and acetone, soluble in methanol, easily soluble in water, 10% aqueous solution pH=4.8～5.0.

解説choline chloride dihydrogen phosphate．C5H15ClNO4P(219.61)．ホスホリルコリンは，ハロゲン化コリンをホスホリルクロリドなどでリン酸化して合成する．酸，アルカリに強く，加水分解されにくい．生体内では，コリンとATPから生成し，CTPと反応してCDPコリンとなり，ジグリセリドと結合してレシチンを生成する．K塩，Cl塩，Ba塩などは肝胆汁機能不全の治療に用いられる．森北出版「化学辞典（第2版）

用途ホスホコリン（phosphocholine）は、組織内におけるホスファチジルコリン合成の中間体である。ホスホコリンはコリンキナーゼ（英語版）によって触媒されるATP + コリンをホスホコリンとADPに変換する反応によって作られる。ホスホコリンは例えばレシチン中に見出される分子である。 ホスホコリンは線虫やヒト胎盤によってホストの免疫応答を抑制するための翻訳後修飾としても用いられる。 また、C反応性蛋白 (CRP) の結合標的の一つである。したがって細胞が損傷を受けた時、CRPはホスホコリンに結合し、認識および食作用免疫応答を開始する。 ホスファチジルコリン (PC) は鶏卵（およびその他の多くの卵）の天然成分の一つであり、Egg-PCの形でしばしば生体模倣膜の研究に使用されている。

説明Phosphorylcholine (abbreviated ChoP) is the hydrophilic polar head group of some phospholipids, which is composed of a negatively charged phosphate bonded to a small, positively charged choline group. It is a choline ester which forms a part of the phosphatide molecule, and as such occurs in nearly all organs. It probably often exists in the free state, being liberated from the phosphatides by enzymic hydrolysis.

使用Phosphocholine is an intermediate in the synthesis of Uridine Diphosphate Choline Ammonium Salt (U829930), which is CDPcholine cholinephosphotransferase analog. Pipeline device with Phosphorylcholine surface treatment (Pipeline Shield) could mitigate device material related thromboembolic complications.

製造方法Phosphorylcholine was synthesised from choline chloride and phosphorus pentoxide, the solvent being 100 percent. phosphoric acid [phosphorylation method of Manaka, 1931]. 2.4 g choline chloride, dried over phosphorus pentoxide, were dissolved in 15 g. 100 per cent. phosphoric acid, the solution was heated at 70°C. in vacuo until evolution of HC1 ceased, and 5 g. phosphorus pentoxide were added. The mixture, which became homogeneous after a few minutes, was kept at 70°C. for 3 hours. The clear viscous solution was poured into 400c.c. of ice water, and a barium hydroxide solution, saturated at 50°C., was added until the solution showed a strongly alkaline reaction. At the end of the neutralisation a smell of trimethylamine appears. The barium phosphate was centrifuged, the excess of barium ions removed by carbon dioxide, the precipitate centrifuged, and the solution reduced in vacuo to a small volume. It still contained a certain amount of barium ions depending on the amount of negatively charged phosphorylcholine ions present. The latter is determined by the pH of the solution. The amount of barium ions present was determined in an aliquot part of the solution by precipitation with sulphuric acid, and the amount of n-sulphuric acid required for complete precipitation of the barium ions added.