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Molecules 2017, 22(8), 1389; doi:10.3390/molecules22081389

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

1
Center for Drug Design, Academic Health Center, University of Minnesota, Minneapolis, MN 55455, USA
2
Division of Applied Bioscience, Graduate School of Agriculture, Hokkaido University, Kita 9, Nishi 9, Kita-ku, Sapporo 060-8589, Japan
*
Author to whom correspondence should be addressed.
Received: 2 August 2017 / Revised: 18 August 2017 / Accepted: 21 August 2017 / Published: 22 August 2017
(This article belongs to the Section Medicinal Chemistry)
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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. View Full-Text
Keywords: photoaffinity labeling; one-pot synthesis; aliphatic diazirine; base-mediated reaction photoaffinity labeling; one-pot synthesis; aliphatic diazirine; base-mediated reaction
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

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.

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