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Base-Mediated One-Pot Synthesis of Aliphatic Diazirines for Photoaffinity Labeling

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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.
Type: article
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)

Submitter: 橋本 誠

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