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Specific Labeling of Mitochondrial Nucleoids for Time-lapse Structured Illumination Microscopy

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Monosaccharide-based water-soluble fluorescent tags.

Alan R Katritzky¹, Janet Cusido, Tamari Narindoshvili

¹Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, Florida 32611-7200, USA. katritzky@chem.ufl.edu

Bioconjugate Chemistry

|June 24, 2008

Summary

This study introduces a novel microwave-assisted method for fluorescently labeling monosaccharides using coumarin derivatives. This efficient technique yields water-soluble fluorescent sugars for potential applications in various scientific fields.

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Highly Sensitive and Rapid Fluorescence Detection with a Portable FRET Analyzer

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Published on: October 1, 2016

Area of Science:

Carbohydrate Chemistry
Organic Synthesis
Fluorescent Probes

Background:

Monosaccharides are fundamental building blocks in biological systems.
Fluorescent labeling of carbohydrates is crucial for biochemical and cellular studies.
Existing labeling methods can be time-consuming or require harsh conditions.

Purpose of the Study:

To develop a rapid and efficient method for fluorescently labeling monosaccharides.
To synthesize novel coumarin-labeled carbohydrate derivatives.
To create water-soluble fluorescent probes from labeled monosaccharides.

Main Methods:

Microwave irradiation was employed for rapid O-acylation and N-acylation reactions.
N-(coumarin-3-carbonyl)benzotriazole was used as the coumarin labeling reagent.
Diisopropylidene-protected monosaccharides and a galactopyranosylamine derivative were utilized.
Coumarin-containing activated lysine derivatives were synthesized and coupled to sugars.

Main Results:

High yields (60-90%) of fluorescently labeled monosaccharides were achieved via O-acylation and N-acylation.
Coumarin-labeled lysine-scaffold based sugars were synthesized with yields of 67-85%.
Removal of protecting groups yielded water-soluble fluorescent carbohydrate derivatives.

Conclusions:

Microwave-assisted synthesis provides an efficient route for coumarin labeling of monosaccharides.
The developed method offers a versatile approach to generating fluorescent carbohydrate probes.
The resulting water-soluble derivatives have potential applications in glycobiology and diagnostics.