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

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Fluorescent Labelling of Glycans with FRET-Based Probes in a Gold(III)-Mediated Three-Component Coupling Reaction.
ChemPlusChem ( IF 3.0 ) Pub Date : 2019-11-07 , DOI: 10.1002/cplu.201900612
Hoi-Yi Sit _{1,

2} , Bin Yang _{1,

2} , Karen Ka-Yan Kung _{1,

2} , John Siu-Lun Tam _{1,

2} , Man-Kin Wong _{1,

2}

Affiliation

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 A3 -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 %.

中文翻译：

金（III）介导的三组分偶联反应中基于FRET的探针对聚糖的荧光标记。

考虑到聚糖在介导生物事件和人类疾病中的关键作用，聚糖的单部位多功能化在生物学研究中非常重要。在本文中，已开发出一种新型的聚糖多功能标记方法，其特征在于使用基于荧光共振能量转移（基于FRET）的探针通过金（III）介导的三组分偶联反应对聚糖进行荧光标记。聚糖氧化成醛，然后与基于FRET的探针进行A3偶联反应，导致荧光炔丙基胺产物的单点形成。标记的聚糖的转化可以通过FRET信号的比例分析来揭示。这种标记方法可实现聚糖的多功能化，具有很高的选择性和66％至69％的转化率。

更新日期：2019-11-07

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