Radiochemical and NMR spectroscopic investigation of the solvent effect on the electrophilic elemental fluorination of L-DOPA:: synthesis of [18F]5-fluoro-L-DOPA

被引:16
作者
Chirakal, R [1 ]
Vasdev, N
Schrobilgen, GJ
Nahmias, C
机构
[1] McMaster Univ, Dept Nucl Med, Hamilton, ON, Canada
[2] Hamilton Hlth Sci Corp, Hamilton, ON L8N 3Z5, Canada
[3] McMaster Univ, Dept Chem, Hamilton, ON L8S 4M1, Canada
关键词
electrophilic fluorination; elemental fluorine; 5-fluoro-L-DOPA; fluorine-18;
D O I
10.1016/S0022-1139(99)00123-2
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Differences in reactivity and selectivity of fluorine in the electrophilic fluorination of 3,4-dihydroxy phenyl-L-alanine (L-DOPA) in different solvents have been exploited to produce mCi quantities of [F-18]5-fluoro-L-DOPA. Proton and C-13 NMR spectroscopy have been used to show that, while the orientation of electrophilic fluorination of L-DOPA in weak acids (trifluoroacetic acid, 10% trifluoroacetic acid in glacial acetic acid and formic acid) is influenced by the electron donating OH groups on the ring, the orientation of electrophilic fluorination of L-DOPA in strong acids (HF and HF/BF3) is mainly influenced by the side-chain. (C) 1999 Elsevier Science S.A. All rights reserved.
引用
收藏
页码:87 / 94
页数:8
相关论文
共 27 条
[1]  
ADAM MJ, 1986, J NUCL MED, V27, P1462
[2]   NUCLEAR MAGNETIC RESONANCE STUDIES OF PROTONATION OF WEAK BASES IN FLUOROSULPHURIC ACID .4. PHENOLS + AROMATIC ETHERS [J].
BIRCHALL, T ;
GILLESPIE, RJ ;
BOURNS, AN ;
SMITH, PJ .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1964, 42 (06) :1433-&
[3]  
BROUWER DM, 1966, RECL TRAV CHIM PAY-B, V85, P109
[4]   SUBSTRATE SELECTIVITY AND ORIENTATION IN AROMATIC-SUBSTITUTION BY MOLECULAR FLUORINE [J].
CACACE, F ;
WOLF, AP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (11) :3639-3641
[5]  
CASELLA V, 1980, J NUCL MED, V21, P750
[6]   Elemental fluorine .1. Synthesis of fluoroaromatic compounds [J].
Chambers, RD ;
Skinner, CJ ;
Hutchinson, J ;
Thomson, J .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (07) :605-609
[7]  
CHIRAKAL R, 1991, APPL RADIAT ISOTOPES, V42, P113
[8]  
CHIRAKAL R, 1986, J NUCL MED, V27, P417
[9]   RADIOFLUORINATION WITH F-18-LABELED ACETYL HYPOFLUORITE - [F-18] L-6-FLUORODOPA [J].
CHIRAKAL, R ;
FIRNAU, G ;
COUSE, J ;
GARNETT, ES .
INTERNATIONAL JOURNAL OF APPLIED RADIATION AND ISOTOPES, 1984, 35 (07) :651-653
[10]   ELECTROPHILIC F-18 FROM A SIEMENS 11-MEV PROTON-ONLY CYCLOTRON [J].
CHIRAKAL, R ;
ADAMS, RM ;
FIRNAU, G ;
SCHROBILGEN, GJ ;
COATES, G ;
GARNETT, ES .
NUCLEAR MEDICINE AND BIOLOGY, 1995, 22 (01) :111-116