Please use this identifier to cite or link to this item:
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
Appears in Collections:Journal/Magazine Article

Open Access Information
Status embargoed access
Embargo End Date 2022-03-31
View full-text via PolyU eLinks SFX Query
Show full item record

Page views

Citations as of May 22, 2022


Citations as of May 26, 2022


Citations as of May 26, 2022

Google ScholarTM



Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.