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Base-Mediated One-Pot Synthesis of Aliphatic Diazirines for Photoaffinity Labeling
This item is licensed under:Creative Commons Attribution 4.0 International
| Title: | Base-Mediated One-Pot Synthesis of Aliphatic Diazirines for Photoaffinity Labeling |
| Authors: | Wang, Lei Browse this author | | Tachrim, Zetryana Puteri Browse this author | | Kurokawa, Natsumi Browse this author | | Ohashi, Fumina Browse this author | | Sakihama, Yasuko Browse this author →KAKEN DB | | Hashidoko, Yasuyuki Browse this author →KAKEN DB | | Hashimoto, Makoto Browse this author →KAKEN DB |
| Keywords: | photoaffinity labeling | | one-pot synthesis | | aliphatic diazirine | | base-mediated reaction |
| Issue Date: | 22-Aug-2017 |
| Publisher: | MDPI |
| Journal Title: | Molecules |
| Volume: | 22 |
| Issue: | 8 |
| Start Page: | 1389 |
| Publisher DOI: | 10.3390/molecules22081389 |
| PMID: | 28829361 |
| Abstract: | Aliphatic 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. |
| Rights: | https://creativecommons.org/licenses/by/4.0/ |
| Type: | article |
| URI: | http://hdl.handle.net/2115/67259 |
| Appears in Collections: | 農学院・農学研究院 (Graduate School of Agriculture / Faculty of Agriculture) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)
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Submitter: 橋本 誠
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