MS Active Fluorescent Tagging Reagents for Glycan Analysis
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Solution Overview
Problem
Current methods for fluorescent labeling of glycans are slow, either providing good fluorescence signals with poor mass spectrometry (MS) signals or vice versa, lacking a combination of rapid reaction times and strong signals for both detection methods.
Innovation Solution
Development of MS active compounds with a tertiary amino group, a highly fluorescent moiety, and a functional group that rapidly reacts with amines, such as isocyanate or succinimidylcarbamate, for rapid fluorescence tagging of glycans and other biomolecules, enhancing both MS and fluorescence signals.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Loss of time
If tagging molecules that react quickly are used, then reaction time is reduced, but MS signal is poor
Solution Approach 1:
The patent creates composite tagging molecules that combine a reactive functional group (for rapid reaction), a fluorescent moiety (for fluorescence detection), and an MS-active group (for mass spectrometry detection). This multi-component structure allows the single reagent to simultaneously provide rapid reaction kinetics, strong fluorescence signal, and enhanced MS signal, resolving the contradiction between reaction speed and MS signal quality.
2Measurement precision
If tagging molecules that give good MS/fluorescence signals are used, then detection sensitivity is improved, but reaction time is slow
Solution Approach 1:
The patent modifies the chemical parameters of the tagging molecules by introducing highly reactive functional groups (such as isocyanate, carbodiimide, or active ester groups) that dramatically increase the reaction rate constant. Simultaneously, the molecules are designed with fluorescent and MS-active moieties to maintain strong detection signals. This parameter optimization allows rapid reaction (completed in minutes rather than hours) while preserving strong detection capabilities.
3Adaptability or versatility
If a combination of MS and fluorescence detection is used, then analytical capability is improved, but currently no single reagent provides both strong signals
Solution Approach 1:
The patent designs universal tagging reagents that perform multiple functions simultaneously: (1) rapid covalent binding to amine groups on biomolecules, (2) providing strong fluorescence emission for optical detection, and (3) containing MS-active moieties that enhance mass spectrometry signal. This multi-functionality allows a single reagent to support both fluorescence and MS detection modalities with strong signals from each, enabling comprehensive analytical capability.
Applied Scientific Principles
This section explains which scientific principles are used to turn an abstract innovation direction into a practical engineering solution.
Function Achieved in This Case
These compounds enable rapid tagging of biomolecules, significantly reducing reaction times from hours to seconds, providing strong MS and fluorescence signals, improving the sensitivity and accuracy of glycan and amino acid analysis.
Implementation Method 1
a highly fluorescent moiety
Implementation Method 2
The tertiary amino group substituent provides a strong MS signal
Implementation Method 3
a functional group that rapidly reacts with amines, such as an isocynanate or succidimidylcarbamate
Data Source
AI summary
Reagents comprising MS active, fluorescent molecules with an activated functionality for reaction with amines useful in tagging biomolecules such as N-glycans and uses thereof are taught and described. In particular, compounds for use as a reagent for rapid fluorescence tagging of biomolecules and enhanced MS signaling are provided. The compounds may have optical centers and therefore may occur in different enantiomeric and diastereomeric configurations. These MS active, fluorescent compounds may have three functional components: (a) a tertiary amino group or other MS active atom; (b) a highly fluorescent moiety, and (c) a reactive group that rapidly reacts with amines. The reactive group provides rapid tagging of desired bio-molecules. The fluorescent moiety provides the fluorescent signal. The tertiary amino group provides the MS signal.