L-[S-methyl-11C]methionine | 60305-58-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: L-[S-methyl-11C]methionine
• 英文别名: [11C]-L-methionine；L-[methyl-11C]methionine；[11C]methionine；L-(methyl-11C)methionine；Methionine C-11；(2S)-2-amino-4-(111C)methylsulfanylbutanoic acid
• CAS: 60305-58-0
• 化学式: C₅H₁₁NO₂S
• 分子量: 148.203
• InChiKey: FFEARJCKVFRZRR-JJZBXVGDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  88.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  [11C]methyl iodide 、 L-高半胱氨酸硫代内酯盐酸盐 在 sodium hydroxide 作用下， 以 水 为溶剂， 145.0 ℃ 、35.0 MPa 条件下， 反应 0.08h， 生成 L-[S-methyl-11C]methionine
  参考文献：
  名称：

  Supercritical Fluid Synthesis and On-Line Preparative Supercritical Fluid Chromatography of 11C-Labelled Compounds in Supercritical Ammonia.

  摘要：

  An automated supercritical fluid synthesis (SFS) system, designed for reaction and on-line preparative supercritical fluid chromatography (SFC) of C-11-labelled (t(1/2) = 20.3 min) compounds in supercritical ammonia, is described. The synthesis and on-line SFC purification of [methyl-C-11]anisole, L-[methyl-C-11]methionine and 4-methoxyphenyl[C-11]guanidine gave a >98% radiochemically pure product within 30 min. [methyl-C-11]Anisole was obtained from reaction of phenol with [C-11]methyl iodide and was used as a model reaction to evaluate the synthetic procedure of the system. 4-Methoxyphenyl[C-11]guanidine was produced by reaction of p-anisidine with [C-11]cyanogen bromide to give the C-11-labelled cyanamide, followed by reaction with ammonia to obtain the C-11-guanidine compound. Both D- and L-[methyl-C-11]methionine were produced by reaction of [C-11]methyl iodide and D- and L-homocysteine thiolactone hydrochloride, respectively. The effect of base concentration on the radiochemical yield and enantiomeric purity of C-11-methionine was investigated, and it was found that 2.5 equiv. of base gave a radiochemical yield >95% with 2-3% racemization. In a typical synthesis and on-line SFC purification of C-11-methionine, a 5 mu A h (45 mu A, 6.6 min) bombardment to produce [C-11]carbon dioxide gave a 3.1 GBq sterile solution of C-11-methionine.

  DOI：

  10.3891/acta.chem.scand.51-0418

文献信息

• Highlighting the versatility of the Tracerlab synthesis modules. Part 2: fully automated production of [11C]-labeled radiopharmaceuticals using a Tracerlab FXC-Pro
  作者：Xia Shao、Raphaël Hoareau、Adam C. Runkle、Louis J. M. Tluczek、Brian G. Hockley、Bradford D. Henderson、Peter J. H. Scott

  DOI：10.1002/jlcr.1937

  日期：2011.12

  Herein, we continue our series of articles showcasing the versatility of the Tracerlab FX synthesis modules by presenting straightforward, fully automated methods for preparing a range of carbon‐11 labeled radiopharmaceuticals using a Tracerlab FXC‐Pro. Strategies for production of [11C]acetate, [11C]carfentanil, [11C]choline, [11C]3‐amino‐4‐[2‐[(di(methyl)amino)methyl]phenyl]sulfanylbenzonitrile ([11C]DASB)

  放射化学领域正在朝着自动合成模块的专用化方向发展，以生产临床放射药物剂量。这样的举动不仅具有许多优势，而且还给放射化学工作者带来了重新配置合成模块的挑战，以生产需要非常规放射化学同时又要保持全自动的放射性药物。在此，我们将继续介绍一系列文章，展示通过使用Tracerlab FX C-Pro制备一系列碳11标记的放射性药物的直接，全自动方法，来展示Tracerlab FX合成模块的多功能性。产生[ 11 C]乙酸盐，[ 11 C]芬太尼，[ 11 C]胆碱，[ 11C] 3-氨基-4- [2-[（（（（二（甲基）氨基）甲基]苯基]硫烷基苄腈（[ 11 C] DASB），（+）-[ 11 C]二氢萜烯嗪（[ 11 C] DTBZ） ，[ 11 C]氟马西尼（[ 11 C] FMZ），间羟基麻黄碱（[ 11 C] HED），[ 11 C]蛋氨酸，[ 11 C] PBR28，[ 11 C]匹兹堡化合物B（[
• High efficiency preparation of L-[S-methyl-11C]methionine by on-column [11C]methylation on C18 Sep-Pak
  作者：Claudio Pascali、Anna Bogni、Ren Iwata、Donatella Decise、Flavio Crippa、Emilio Bombardieri

  DOI：10.1002/(sici)1099-1344(199908)42:8<715::aid-jlcr224>3.0.co;2-3

  日期：1999.8

  A novel approach to the synthesis of L-[S-methyl-11C]methionine ([11C]MET) is described which involves a commercial C18 Sep-Pak Plus as a solid-phase support material for the [11C]methylation step. The present method, which uses [11C]CH3I produced by the classical LiA1H4/HI route, supplies [11C]MET ready for injection within 11 min from the end of bombardment (EOB) with a radiochemical yield, decay

  描述了一种合成 L-[S-甲基-11C] 甲硫氨酸 ([11C]MET) 的新方法，该方法涉及商业 C18 Sep-Pak Plus 作为 [11C] 甲基化步骤的固相支持材料。本方法使用由经典 LiAlH4/HI 路线产生的 [11C]CH3I，在轰击 (EOB) 结束后 11 分钟内提供准备注射的 [11C]MET，放射化学产率在 EOB 处校正衰减为 78 % 并且合成结束时的放射化学纯度 (EOS) 高于 99%。所需的设置非常简单且易于自动化，并且可以在几分钟内重置以进行进一步的合成。此外，由于其多功能性，该方法可用于生产其他需要简单 [11C] 甲基化的放射性药物。版权所有 © 1999 John Wiley & Sons, Ltd.
• Methylation of amide and thiol functions with [11C]methyl triflate, as exemplified by [11C]NMSP[11C]flumazenil and [11C]methionine
  作者：Kjell Någren、Christer Halldin

  DOI：10.1002/(sici)1099-1344(1998090)41:9<831::aid-jlcr129>3.0.co;2-e

  日期：1998.9
• Pascali; Bogni; Iwata, Journal of labelled compounds and radiopharmaceuticals, 1999, vol. 42, # SUPPL. 1, p. S474-S476
  作者：Pascali、Bogni、Iwata、Decise、De Sanctis、Chiesa、Crippa、Bombardieri

  DOI：——

  日期：——
• STEINBACH, J.;BEYER, G. -J.;GUNTHER, K., ZENTRALINST. KERNFORSCH. ROSSENDORF DRESDEN. <BER.>,(1989) N69, C. 28-29
  作者：STEINBACH, J.、BEYER, G. -J.、GUNTHER, K.

  DOI：——

  日期：——