Department of Chemistry, Princeton University , Princeton, New Jersey 08544, United States.
J Am Chem Soc. 2014 May 14;136(19):6842-5. doi: 10.1021/ja5039819. Epub 2014 May 6.
We describe the first late-stage (18)F labeling chemistry for aliphatic C-H bonds with no-carrier-added [(18)F]fluoride. The method uses Mn(salen)OTs as an F-transfer catalyst and enables the facile labeling of a variety of bioactive molecules and building blocks with radiochemical yields (RCY) ranging from 20% to 72% within 10 min without the need for preactivation of the labeling precursor. Notably, the catalyst itself can directly elute [(18)F]fluoride from an ion exchange cartridge with over 90% efficiency. Using this feature, the conventional and laborious dry-down step prior to reaction is circumvented, greatly simplifying the mechanics of this protocol and shortening the time for automated synthesis. Eight drug molecules, including COX, ACE, MAO, and PDE inhibitors, have been successfully [(18)F]-labeled in this way.
我们描述了首例使用无载体添加的 [(18)F] 氟化物对脂肪族 C-H 键进行晚期（18）F 标记化学的方法。该方法使用 Mn(salen)OTs 作为 F-转移催化剂，能够在 10 分钟内轻松标记各种生物活性分子和构建块，放射性化学收率（RCY）范围为 20%至 72%，而无需对标记前体进行预激活。值得注意的是，催化剂本身可以直接从离子交换柱中以超过 90%的效率洗脱 [(18)F] 氟化物。利用这一特性，可以避免在反应前进行传统且繁琐的干燥步骤，极大地简化了该方案的操作，并缩短了自动化合成的时间。通过这种方式，已经成功地对八种药物分子（包括 COX、ACE、MAO 和 PDE 抑制剂）进行了 [(18)F] 标记。
