Please use this identifier to cite or link to this item:
http://hdl.handle.net/10397/89273
| 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 |
Files in This Item:
| File | Description | Size | Format | |
|---|---|---|---|---|
| Ko_Modification_Alkyne-linked_Peptides.pdf | Pre-Published version | 1.18 MB | Adobe PDF | View/Open |
Access
View full-text via PolyU eLinks 
Page views
41
Last Week
0
0
Last month
Citations as of Sep 24, 2023
Downloads
5
Citations as of Sep 24, 2023
SCOPUSTM
Citations
11
Citations as of Sep 28, 2023
WEB OF SCIENCETM
Citations
11
Citations as of Sep 28, 2023
Google ScholarTM
Check
Altmetric
Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.