Lignin Derivatization for Monolignol Ester Conjugate Detection

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Solution Overview

Problem

Current methods lack the ability to effectively detect and quantify the incorporation of monolignol ester conjugates into plant lignin, which are crucial for designing plants with improved processing properties for biofuels and paper production.

Innovation Solution

A method involving derivatization of lignin to acylate and halogenate specific groups, followed by reduction and acetylation with labeled reagents to detect and quantify monolignol ester conjugates using chromatography and mass spectrometry.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Measurement precision

If conventional detection methods are used, then the process is simple, but the ability to detect and quantify monolignol ester conjugates is insufficient

Engineering Contradiction:
Improvedetection capabilityVSAvoidmethod complexity
Core Design Contradiction:
Measurement precisionVSDevice complexity

Solution Approach 1:

The method applies preliminary derivatization steps (acylation and halogenation) to the lignin sample before detection. These preliminary actions modify the monolignol ester conjugates to introduce detectable labels and improve their analytical properties, enabling subsequent precise quantification that would not be possible with conventional direct detection methods

Inventive Principle:
Principle #10Preliminary action

Solution Approach 2:

The patent uses labeled reagents as intermediaries to detect the monolignol ester conjugates. The labeling process introduces detectable markers that act as mediators between the target analyte and the detection system, significantly enhancing the measurement precision while managing the complexity through systematic chemical transformation

Inventive Principle:
Principle #24Intermediary (Mediator)

2Loss of information

If no specific detection method is used, then the method is simple, but the quantification of incorporation levels is not possible

Engineering Contradiction:
Improveinformation on incorporation levelsVSAvoiddetection difficulty
Core Design Contradiction:
Loss of informationVSDifficulty of detecting and measuring

Solution Approach 1:

The method employs labeled reagents that introduce detectable signals (analogous to color changes in spectroscopic detection) to the monolignol ester conjugates. This transformation enables the detection system to distinguish and quantify the incorporated conjugates based on their unique spectral or mass characteristics, preventing information loss about incorporation levels

Inventive Principle:
Principle #32Color changes

Solution Approach 2:

The patent changes the physical-chemical parameters of the target molecules through derivatization, transforming them into forms with distinct detectable properties. This parameter change enables the detection system to measure incorporation levels by detecting the introduced labels, overcoming the difficulty of directly measuring the native conjugates

Inventive Principle:
Principle #35Parameter changes

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

Enables the unambiguous detection and quantification of monolignol ester conjugates in lignin, facilitating the development of plants with tailored processing properties by determining their incorporation levels.

Implementation Method 1

treating the derivatized lignin with a reducing agent to cleave at least a portion of the derivatized lignin

Methodology Applied
Scientific EffectReduction: Reduction

Implementation Method 2

acetylating at least a portion of free hydroxyl groups in the lignin cleavage products with a labeled acetylation agent

Methodology Applied
Scientific EffectAcetylation: Chemical Bonding

Data Source

PatentUS11414372B2Methods for detecting and determining levels of monolignol ester conjugates incorporated into lignin and compounds relating thereto
Publication Date: 2022.08.16 WISCONSIN ALUMNI RES FOUND
  • US11414372B2 patent drawing
  • US11414372B2 patent drawing
  • US11414372B2 patent drawing

AI summary

Methods of detecting and, optionally, determining a level of incorporation of monolignol ester conjugates into lignin. The methods include derivatizing lignin to acylate at least a portion of free phenolic and aliphatic hydroxyls and to halogenate at least a portion of benzylic alcohols present in the lignin to yield derivatized lignin, treating the derivatized lignin with a reducing agent to cleave at least a portion of the derivatized lignin to yield lignin cleavage products, acetylating at least a portion of free hydroxyl groups in the lignin cleavage products with a labeled acetylation agent to yield labeled lignin fragments, and detecting the labeled lignin fragments.