Fluorescent Labelling of Glycans with FRET-Based Probes in a Gold(III)-Mediated Three-Component Coupling Reaction.

Autor: Sit HY; The Hong Kong Polytechnic University, Shenzhen Research Institute, Shenzhen, P. R. China.; State Key Laboratory of Chemical Biology and Drug Discovery and Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hung Hom, Hong Kong, P. R. China., Yang B; The Hong Kong Polytechnic University, Shenzhen Research Institute, Shenzhen, P. R. China.; State Key Laboratory of Chemical Biology and Drug Discovery and Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hung Hom, Hong Kong, P. R. China., Ka-Yan Kung K; The Hong Kong Polytechnic University, Shenzhen Research Institute, Shenzhen, P. R. China.; State Key Laboratory of Chemical Biology and Drug Discovery and Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hung Hom, Hong Kong, P. R. China., Siu-Lun Tam J; The Hong Kong Polytechnic University, Shenzhen Research Institute, Shenzhen, P. R. China.; State Key Laboratory of Chemical Biology and Drug Discovery and Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hung Hom, Hong Kong, P. R. China., Wong MK; The Hong Kong Polytechnic University, Shenzhen Research Institute, Shenzhen, P. R. China.; State Key Laboratory of Chemical Biology and Drug Discovery and Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hung Hom, Hong Kong, P. R. China.
Jazyk: angličtina
Zdroj: ChemPlusChem [Chempluschem] 2019 Nov; Vol. 84 (11), pp. 1739-1743. Date of Electronic Publication: 2019 Nov 07.
DOI: 10.1002/cplu.201900612
Abstrakt: Single-site multifunctionalization of glycans is of importance in biological studies considering its crucial role in mediating biological events and human diseases. In this paper, a novel approach for multifunctional labelling of glycans has been developed featuring the use of fluorescence resonance energy transfer-based (FRET-based) probes for fluorescent labelling of glycans through a gold(III)-mediated three-component coupling reaction. Oxidation of glycans into aldehydes followed by the A 3 -coupling reaction with FRET-based probes resulted in the single-site formation of fluorescent propargylamine products. The conversion of labelled glycans can be revealed by ratiometric analysis of the FRET signals. This labelling approach results in multifunctionalization of glycans with high selectivity and conversion between 66 and 69 %.
(© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.)
Databáze: MEDLINE
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