Guo Hai-Ming, Tanaka Fujie
Department of Molecular Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
J Org Chem. 2009 Mar 20;74(6):2417-24. doi: 10.1021/jo900013w.
We have developed a new type of fluorogenic aldehyde bearing a 1,2,3-triazole moiety that is useful for monitoring the progress of aldol reactions through an increase in fluorescence. Whereas 6-methoxy-2-naphthaldehyde was highly fluorescent, the fluorogenic aldehyde, 4-formylbenzene connected to the 6-methoxy-2-naphthyl group through a 1,2,3-triazole moiety, was essentially nonfluorescent in aqueous solutions. We suggest that the 4-formylphenyl group acts as a quencher to suppress the fluorescence of the 6-methoxy-2-naphthyltriazole moiety. The product of the aldol reaction of this aldehyde does not have a quenching moiety and showed more than 800-fold higher fluorescence than the aldehyde. Assay systems using the fluorogenic aldehyde were validated by screening of aldol catalysts, ranking of the activities of the catalysts, and evaluation of reaction conditions.
我们开发了一种新型的带有1,2,3-三唑部分的荧光醛,它可用于通过荧光增强来监测羟醛反应的进程。6-甲氧基-2-萘甲醛具有高荧光性,而通过1,2,3-三唑部分连接到6-甲氧基-2-萘基的荧光醛4-甲酰基苯在水溶液中基本无荧光。我们认为4-甲酰基苯基起到淬灭剂的作用,抑制了6-甲氧基-2-萘基三唑部分的荧光。该醛的羟醛反应产物没有淬灭部分,其荧光比醛高出800多倍。使用该荧光醛的检测系统通过筛选羟醛催化剂、对催化剂活性进行排序以及评估反应条件得到了验证。