6-[18F]fluoro-D-3,4-dihydroxy phenylalanine

• 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: 6-[18F]fluoro-D-3,4-dihydroxy phenylalanine
• 英文别名: [18F]-D-3,4-dihydroxy-6-fluorophenylalanine；6-<18F>fluoro-D-DOPA；[18F]6-fluoro-L-dopa；6-[18F]fluoro-D-DOPA；(2R)-2-amino-3-(2-(18F)fluoranyl-4,5-dihydroxyphenyl)propanoic acid
• 化学式: C₉H₁₀FNO₄
• 分子量: 214.183
• InChiKey: PAXWQORCRCBOCU-CDSXIGCZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  104
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  6-<(18)F>fluoro-L-DOPA 生成 6-[18F]fluoro-D-3,4-dihydroxy phenylalanine
  参考文献：
  名称：

  LEMAIRE, CHRISTIAN;GUILLAUME, MARCEL;CANTINEAU, ROBERT;CHRISTIAENS, LEON, J. NUCL. MED., 31,(1990) N, C. 1247-1251

  摘要：

  DOI：

文献信息

• No-carrier-added (NCA) synthesis of 6-[18F]fluoro-L-DOPA using 3,5,6,7,8,8a-hexahydro-7,7,8a-trimethyl-[6s-(6α,8α,8αβ)]-6,8-methano-2H-1,4-benzoxazin-2-one
  作者：Andrew Horti、D. Eugene Redmond、Robert Soufer

  DOI：10.1002/jlcr.2580360503

  日期：1995.5

  8a-trimethyl-[6S-(6α,8α,8αβ)]-6,8-methano-2H-1,4-benzoxazino-2-one (2) was investigated as chiral auxiliary for asymmetric NCA nucleophilic synthesis of 6-[ 18 F]Fluoro-L-DOPA. Direct condensation of 3,4-dimethoxy-2-[ 18 F]fluorobenzaldehyde (1a) or 6-[ 18 F]fluoropiperonal (1b) in the presence of NaH with 2 gave the corresponding [ 18 F]-3-[(2-fluorophenyl)methylene]-3,5,6,7,8,8a-hexahydro-7,7,8a-trimethyl-[6S-(3Z

  3,5,6,7,8,8a-Hexahydro-7,7,8a-trimethyl-[6S-(6α,8α,8αβ)]-6,8-methano-2H-1,4-benzoxazino-2-一 (2) 被研究作为 6-[ 18 F] 氟-L-DOPA 的不对称 NCA 亲核合成的手性助剂。3,4-二甲氧基-2-[ 18 F] 氟苯甲醛 (1a) 或 6-[ 18 F] 氟胡椒醛 (1b) 在 NaH 存在下与 2 直接缩合得到相应的 [ 18 F]-3-[(2 -氟苯基)亚甲基]-3,5,6,7,8,8a-六氢-7,7,8a-三甲基-[6S-(3Z,3α,6α,8α,8αβ)]-6,8-methano- 2H-1,4-benzoxazin-2-one 衍生物 3a 或 3b 作为单一立体异构体。L-Selectride® 在叔丁醇存在下促进这些衍生物的烯属双键的氢化，得到相应的 [ 18 F]-3-[(2-氟苯基)甲基]-3
• Trifluoromethanesulfonic acid, an alternative solvent medium for the direct electrophilic fluorination of DOPA: new syntheses of 6-[18F]fluoro-L-DOPA and 6-[18F]fluoro-D-DOPA
  作者：Babak Behnam Azad、Raman Chirakal、Gary J. Schrobilgen

  DOI：10.1002/jlcr.1454

  日期：2007.12

  Previous work from this laboratory has shown that the direct fluorination of 3, 4-dihydroxy-phenyl-L-alanine (L-DOPA) in anhydrous HF (aHF) or BF3/HF with F2 is an efficient method for the synthesis of 6-fluoro-L-DOPA. Since then, 18F-labeled 6-fluoro-L-DOPA ([18F]6-fluoro-L-DOPA) has been used to study presynaptic dopaminergic function in the human brain and to monitor gastrointestinal carcinoid tumors. This work demonstrates that the reactivity and selectivity of F2 toward L-DOPA in CF3SO3H is comparable with that in aHF. This new synthetic procedure has led to the production of [18F]fluoro-L-DOPA and [18F]fluoro-D-DOPA isomers in 17±2% radiochemical yields (decay corrected with respect to [18F]F2). The 2- and 6-FDOPA isomers were separated by HPLC and subsequently characterized by 19F NMR spectroscopy. The corresponding [18F]-FDOPA enantiomers have been obtained in clinically useful quantities by a synthetic approach that avoids the use of aHF. Copyright © 2007 John Wiley & Sons, Ltd.

  该实验室之前的研究表明，在无水氢氟酸（aHF）或 BF3/HF 中用 F2 直接氟化 3，4-二羟基苯基-L-丙氨酸（L-DOPA）是合成 6-氟-L-DOPA 的有效方法。此后，18F 标记的 6-氟-L-DOPA（[18F]6-氟-L-DOPA）被用于研究人脑突触前多巴胺能功能和监测胃肠道类癌。 这项研究表明，F2 在 CF3SO3H 中对 L-DOPA 的反应性和选择性与在 aHF 中相当。这一新的合成过程产生了[18F]氟-L-DOPA和[18F]氟-D-DOPA异构体，放射化学收率为17±2%（相对于[18F]F2的衰变校正）。2-FDOPA 和 6-FDOPA 异构体通过高效液相色谱法分离，随后通过 19F NMR 光谱法进行表征。相应的 [18F]-FDOPA 对映异构体已通过避免使用 aHF 的合成方法获得了临床有用的数量。Copyright © 2007 John Wiley & Sons, Ltd. All Rights Reserved.
• Schubiger, P. A.; Krasikova, R.; Zaitsev, V., Journal of labelled compounds and radiopharmaceuticals, 2003, vol. 46, p. S19 - S19
  作者：Schubiger, P. A.、Krasikova, R.、Zaitsev, V.、Kuznetsova, O.、Fedorova, O.、Mosevich, I.、Ametamey, S. M.、Belokon, Y.、Vyskocil, S.

  DOI：——

  日期：——
• Krasikova; Fedorova; Mosevich, Journal of labelled compounds and radiopharmaceuticals, 1999, vol. 42, # SUPPL. 1, p. S102-S104
  作者：Krasikova、Fedorova、Mosevich、Kuznetsova、Korsakov、Ametamey、Schubiger

  DOI：——

  日期：——
• LEMAIRE, CHRISTIAN;GUILLAUME, MARCEL;CANTINEAU, ROBERT;CHRISTIAENS, LEON, J. NUCL. MED., 31,(1990) N, C. 1247-1251
  作者：LEMAIRE, CHRISTIAN、GUILLAUME, MARCEL、CANTINEAU, ROBERT、CHRISTIAENS, LEON

  DOI：——

  日期：——