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| Title: | Selective modification of alkyne-linked peptides and proteins by cyclometalated gold(III) (C^N) complex-mediated alkynylation | Authors: | Ko, HM Deng, JR Cui, JF Kung, KKY Leung, YC Wong, MK |
Issue Date: | 1-Apr-2020 | Source: | Bioorganic & medicinal chemistry, 1 Apr. 2020, v. 28, no. 7, 115375 | Abstract: | Alkyne is a useful functionality incorporated in proteins for site-selective bioconjugation reactions. Although effective bioconjugation reactions such as copper(I)-catalyzed and/or copper-free 1,3-dipolar cycloadditions of alkynes and azides are the most common approaches, the development of new alkyne-based bioconjugation reactions is still an ongoing interest in chemical biology. In this work, a new approach has been developed for selective modification of alkyne-linked peptides and proteins through the formation of arylacetylenes by a cross-coupling reaction of 6-membered ring cyclometalated gold(III) (C^N) complexes (HC^N = 2-arylpyridines) with terminal alkynes. Screening of the reaction conditions with a series of cyclometalated gold(III) complexes with phenylacetylene gave an excellent yield (up to 82%) by conducting the reaction in slightly alkaline aqueous conditions. The reaction scope was expanded to various alkynes, including alkyne-linked peptides to achieve up to >99% conversion. Using fluorescent dansyl (1l) and BODIPY (1m)-linked gold(III) complexes, alkyne-linked lysozyme has been selectively modified. | Keywords: | Alkynylation Bioconjugation reaction Gold complexes Protein modification |
Publisher: | Pergamon Press | Journal: | Bioorganic & medicinal chemistry | ISSN: | 0968-0896 | EISSN: | 1464-3391 | DOI: | 10.1016/j.bmc.2020.115375 | Rights: | © 2020 Elsevier Ltd. All rights reserved © 2020. This manuscript version is made available under the CC-BY-NC-ND 4.0 license http://creativecommons.org/licenses/by-nc-nd/4.0/. The following publication Ko, H.-M., Deng, J.-R., Cui, J.-F., Kung, K. K.-Y., Leung, Y.-C., & Wong, M.-K. (2020). Selective modification of alkyne-linked peptides and proteins by cyclometalated gold(III) (C^N) complex-mediated alkynylation. Bioorganic & Medicinal Chemistry, 28(7), 115375 is available at https://dx.doi.org/10.1016/j.bmc.2020.115375. |
| Appears in Collections: | Journal/Magazine Article |
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