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

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 synthes...

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Autores principales: Wang, Lei, Tachrim, Zetryana Puteri, Kurokawa, Natsumi, Ohashi, Fumina, Sakihama, Yasuko, Hashidoko, Yasuyuki, Hashimoto, Makoto
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2017
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6152361/
https://www.ncbi.nlm.nih.gov/pubmed/28829361
http://dx.doi.org/10.3390/molecules22081389
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author Wang, Lei
Tachrim, Zetryana Puteri
Kurokawa, Natsumi
Ohashi, Fumina
Sakihama, Yasuko
Hashidoko, Yasuyuki
Hashimoto, Makoto
author_facet Wang, Lei
Tachrim, Zetryana Puteri
Kurokawa, Natsumi
Ohashi, Fumina
Sakihama, Yasuko
Hashidoko, Yasuyuki
Hashimoto, Makoto
author_sort Wang, Lei
collection PubMed
description 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.
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spelling pubmed-61523612018-11-13 Base-Mediated One-Pot Synthesis of Aliphatic Diazirines for Photoaffinity Labeling Wang, Lei Tachrim, Zetryana Puteri Kurokawa, Natsumi Ohashi, Fumina Sakihama, Yasuko Hashidoko, Yasuyuki Hashimoto, Makoto Molecules Article 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. MDPI 2017-08-22 /pmc/articles/PMC6152361/ /pubmed/28829361 http://dx.doi.org/10.3390/molecules22081389 Text en © 2017 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Wang, Lei
Tachrim, Zetryana Puteri
Kurokawa, Natsumi
Ohashi, Fumina
Sakihama, Yasuko
Hashidoko, Yasuyuki
Hashimoto, Makoto
Base-Mediated One-Pot Synthesis of Aliphatic Diazirines for Photoaffinity Labeling
title Base-Mediated One-Pot Synthesis of Aliphatic Diazirines for Photoaffinity Labeling
title_full Base-Mediated One-Pot Synthesis of Aliphatic Diazirines for Photoaffinity Labeling
title_fullStr Base-Mediated One-Pot Synthesis of Aliphatic Diazirines for Photoaffinity Labeling
title_full_unstemmed Base-Mediated One-Pot Synthesis of Aliphatic Diazirines for Photoaffinity Labeling
title_short Base-Mediated One-Pot Synthesis of Aliphatic Diazirines for Photoaffinity Labeling
title_sort base-mediated one-pot synthesis of aliphatic diazirines for photoaffinity labeling
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6152361/
https://www.ncbi.nlm.nih.gov/pubmed/28829361
http://dx.doi.org/10.3390/molecules22081389
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