Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA.
Bioorg Med Chem Lett. 2011 May 1;21(9):2702-5. doi: 10.1016/j.bmcl.2010.11.122. Epub 2010 Dec 4.
Alkynyl- and azido-tagged 3-oxo-C(12)-acylhomoserine lactone probes have been synthesized to examine their potential utility as probes for discovering the mammalian protein target of the Pseudomonas aeruginosa autoinducer, 3-oxo-C(12)-acylhomoserine lactone. Although such substitutions are commonly believed to be quite conservative, from these studies, we have uncovered a drastic difference in activity between the alkynyl- and azido-modified compounds, and provide an example where such structural modification has proved to be much less than conservative.
炔基-和叠氮基标记的 3-氧代-C(12)-酰基高丝氨酸内酯探针已被合成,以研究它们作为发现铜绿假单胞菌自动诱导物,3-氧代-C(12)-酰基高丝氨酸内酯的哺乳动物蛋白靶标的探针的潜在用途。尽管这种取代通常被认为是相当保守的,但通过这些研究,我们发现炔基-和叠氮基修饰化合物之间的活性有很大差异,并提供了一个例子,证明这种结构修饰远非保守。