Department of Oncology, University of Alberta, 11560 University Ave, Edmonton, AB T6G 1Z2, Canada.
Org Biomol Chem. 2010 Oct 21;8(20):4730-5. doi: 10.1039/c0ob00255k. Epub 2010 Aug 25.
A novel synthesis of 4-[(18)F]fluorobenzylamine ([(18)F]FBA) by means of transition metal-assisted sodium borohydride reduction of 4-[(18)F]fluorobenzonitrile ([(18)F]FBN) is described. This approach could successfully be extended to borohydride exchange resin (BER) enabling a viable option for use in automated syntheses. [(18)F]FBA was used for the synthesis of 4-[(18)F]fluorobenzylamine-based thiol group-reactive prosthetic groups 4-[(18)F]fluorobenzyl-2-bromoacetamide ([(18)F]FBBA) and 4-[(18)F]fluorobenzylamidopropionyl maleimide ([(18)F]FBAPM). [(18)F]FBBA and [(18)F]FBAPM were obtained in radiochemical yields of 75% and 55%, respectively. Feasibility of using [(18)F]FBAPM as novel prosthetic group for peptide and protein labelling was demonstrated with cysteine-containing tripeptide glutathione (GSH). [(18)F]FBBA was used for labelling of a fully phosphorothioated 20mer oligodesoxynucleotide (ODN).
介绍了一种通过过渡金属辅助的硼氢化钠还原 4-[(18)F]氟苯甲腈([(18)F]FBN)合成 4-[(18)F]氟苯甲胺([(18)F]FBA)的新方法。该方法可以成功地扩展到硼氢化钠交换树脂（BER），为自动化合成提供了可行的选择。[(18)F]FBA 用于合成 4-[(18)F]氟苯甲胺基巯基反应性取代基 4-[(18)F]氟苯甲酰-2-溴乙酰胺([(18)F]FBBA)和 4-[(18)F]氟苯甲酰胺丙酰基马来酰亚胺([(18)F]FBAPM)。[(18)F]FBBA 和 [(18)F]FBAPM 的放射化学产率分别为 75%和 55%。用含有半胱氨酸的三肽谷胱甘肽（GSH）证明了[(18)F]FBAPM 作为新型肽和蛋白质标记取代基的可行性。[(18)F]FBBA 用于完全硫代磷酸化的 20 mer 寡脱氧核苷酸（ODN）的标记。
