No-carrier-added asymmetric synthesis of alpha-methyl-alpha-amino acids labelled with fluorine-18

被引：16

作者：

Damhaut, P ^{[1
]}

Lemaire, C ^{[1
]}

Plenevaux, A ^{[1
]}

Brihaye, C ^{[1
]}

Christiaens, L ^{[1
]}

Comar, D ^{[1
]}

机构：

[1] UNIV LIEGE,CYCLOTRON RES CTR,B-4000 LIEGE,BELGIUM

来源：

TETRAHEDRON | 1997年 / 53卷 / 16期

关键词：

D O I：

10.1016/S0040-4020(97)00265-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Various [F-18]fluoro aromatic alpha-methyl-L-amino acids 11 have been synthesized with high enantiomeric purity tee > 97%). These new radiopharmaceuticals for Positron Emission Tomography (PET), potential inhibitors of enzymatic functions, were regiospecifically labelled by nucleophilic substitution on trimethylammoniumbenzaldehyde triflate precursors 9. The [F-18]fluoro aromatic aldehydes 12 obtained were easily converted to the corresponding [F-18]fluorobenzyl halides [13 (X = I)]. After alkylation of the lithium enolate of (2S,5S)-1-tert-Boc-2-tert-butyl-3,5-dimethyl-imidazolidin-4-one 2, the adducts were cleaved to give, after HPLC purification, various [F-18]fluoro-alpha-methyl amino acid analogs with radiochemical yields of 10% (End of Bombardment, EOB) after a synthesis time of 120 min. The corresponding [F-19]fluorinated amino acids 4 and [F-19]fluoro intermediates were also prepared. (C) 1997 Elsevier Science Ltd.

引用

页码：5785 / 5796

页数：12

共 31 条

[1] Enantioselective syntheses of no-carrier-added (nca) (S)-4-chloro-2[F-18]fluorophenylalanine and (S)-(alpha-methyl)-4-chloro-2[F-18]fluorophenylalanine [J].