Base-Mediated One-Pot Synthesis of Aliphatic Diazirines for Photoaffinity Labeling
AbstractAliphatic diazirines have been widely used as prominent photophores for photoaffinity labeling owing to their relatively small size which can reduce the steric effect on the natural interaction between ligands and proteins. Based on our continuous efforts to develop efficient methods for the synthesis of aliphatic diazirines, we present here a comprehensive study about base-mediated one-pot synthesis of aliphatic diazirines. It was found that potassium hydroxide (KOH) can also promote the construction of aliphatic diazirine with good efficiency. Importantly, KOH is cheaper, highly available, and easily handled and stored compared with the previously used base, potassium tert-butoxide (t-BuOK). Gram-scale study showed that it owned great advantages in being used for the large-scale production of aliphatic diazirines. This protocol is highly neat and the desired products can be easily isolated and purified. As the first comprehensive study of the base-mediated one-pot synthesis of aliphatic diazirines, this work provided good insight into the preparation and utilization of diazirine-based photoaffinity labeling probes. View Full-Text
- Supplementary File 1:
Supplementary (PDF, 571 KB)
Share & Cite This Article
Wang, L.; Tachrim, Z.P.; Kurokawa, N.; Ohashi, F.; Sakihama, Y.; Hashidoko, Y.; Hashimoto, M. Base-Mediated One-Pot Synthesis of Aliphatic Diazirines for Photoaffinity Labeling. Molecules 2017, 22, 1389.
Wang L, Tachrim ZP, Kurokawa N, Ohashi F, Sakihama Y, Hashidoko Y, Hashimoto M. Base-Mediated One-Pot Synthesis of Aliphatic Diazirines for Photoaffinity Labeling. Molecules. 2017; 22(8):1389.Chicago/Turabian Style
Wang, Lei; Tachrim, Zetryana Puteri; Kurokawa, Natsumi; Ohashi, Fumina; Sakihama, Yasuko; Hashidoko, Yasuyuki; Hashimoto, Makoto. 2017. "Base-Mediated One-Pot Synthesis of Aliphatic Diazirines for Photoaffinity Labeling." Molecules 22, no. 8: 1389.
Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.