A “Catch‐and‐Release” Protocol for Alkyne‐Tagged Molecules Based on a Resin‐Bound Cobalt Complex for Peptide Enrichment in Aqueous Media |
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Authors: | Dr Ayako Miyazaki Dr Miwako Asanuma Dr Kosuke Dodo Dr Hiromichi Egami Prof?Dr Mikiko Sodeoka |
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Institution: | 1. Sodeoka Live Cell Chemistry Project, ERATO, Japan Science and Technology Agency (JST), 2‐1 Hirosawa, Wako, Saitama 351‐0198 (Japan) and Synthetic Organic Chemistry Laboratory, RIKEN, 2‐1 Hirosawa, Wako, Saitama 351‐0198 (Japan);2. Current address: Institute of Transformative, Bio‐Molecules (WPI‐ITbM), Nagoya University, Furo‐cho, Chikusa‐ku, Nagoya 464‐8601 (Japan);3. Current address: School of Pharmaceutical Sciences, University of Shizuoka, 52‐1 Yada, Suruga‐ku, Shizuoka 422‐8526 (Japan);4. RIKEN Center for Sustainable Resource Science, 2‐1 Hirosawa, Wako, Saitama 351‐0198 (Japan) |
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Abstract: | The development of new and mild protocols for the specific enrichment of biomolecules is of significant interest from the perspective of chemical biology. A cobalt–phosphine complex immobilised on a solid‐phase resin has been found to selectively bind to a propargyl carbamate tag, that is, “catch”, under dilute aqueous conditions (pH 7) at 4 °C. Upon acidic treatment of the resulting resin‐bound alkyne–cobalt complex, the Nicholas reaction was induced to “release” the alkyne‐tagged molecule from the resin as a free amine. Model studies revealed that selective enrichment of the alkyne‐tagged molecule could be achieved with high efficiency at 4 °C. The proof‐of‐concept was applied to an alkyne‐tagged amino acid and dipeptide. Studies using an alkyne‐tagged dipeptide proved that this protocol is compatible with various amino acids bearing a range of functionalities in the side‐chain. In addition, selective enrichment and detection of an amine derived from the “catch and release” of an alkyne‐tagged dipeptide in the presence of various peptides has been accomplished under highly dilute conditions, as determined by mass spectrometry. |
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Keywords: | alkynes cobalt peptides solid‐phase synthesis |
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