Sialic Acid Esterification Amidation Glycan Analysis

Resolve Bottlenecks,
Find Innovative Solutions
Generate Solutions

Solution Overview

Problem

Current methods for modifying sialic acids in glycans for analysis are limited by the instability of lactones and the inability to achieve linkage-specific modification efficiently.

Innovation Solution

A method involving esterification reactions that modify sialic acids without lactonization, followed by amidation reactions using specific compounds like ammonia, amines, or their salts, to convert esterified sialic acids into amidated forms in a linkage-specific manner.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Manufacturing precision

If lactonization is used to modify sialic acid, then linkage-specific modification is enabled, but the lactone structure becomes extremely unstable and easily hydrolyzed

Engineering Contradiction:
Improvelinkage-specific modificationVSAvoidlactone stability
Core Design Contradiction:
Manufacturing precisionVSStability of the object's composition

Solution Approach 1:

The patent uses an intermediary approach by first forming the lactone structure for linkage-specific identification, then stabilizing it through conversion to a more stable derivative form. The lactone acts as a temporary intermediary that enables specific detection while the stabilization step preserves the analytical information.

Inventive Principle:
Principle #24Intermediary (Mediator)

Solution Approach 2:

The patent performs preliminary lactonization to establish linkage-specific modification before the structure becomes unstable. This preliminary action creates a detectable marker that can then be stabilized for subsequent analysis, ensuring the linkage information is captured before degradation occurs.

Inventive Principle:
Principle #10Preliminary action

2Measurement precision

If multiple modification steps are performed to achieve linkage-specific analysis, then analysis precision is improved, but the procedure becomes complex and time-consuming

Engineering Contradiction:
Improvelinkage analysis precisionVSAvoidprocedure complexity
Core Design Contradiction:
Measurement precisionVSDevice complexity

Solution Approach 1:

The patent merges multiple modification steps into a integrated workflow where lactonization, stabilization, and detection are combined in a coordinated sequence. This merging reduces the number of separate operations required while maintaining the precision benefits of multi-step modification.

Inventive Principle:
Principle #5Merging (Combining)

Solution Approach 2:

The patent optimizes reaction parameters such as pH, temperature, and reagent concentrations to enable efficient modification under controlled conditions. By carefully adjusting these parameters, the procedure achieves high precision while minimizing unnecessary steps and reducing overall complexity.

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

This method allows for the efficient and linkage-specific modification of sialic acids, enhancing the analysis of glycans by improving the stability and distinguishability of modified sialic acid forms.

Implementation Method 1

performing esterification reaction that subjects at least a part of a sialic acid included in the glycan to esterification other than lactonization

Methodology Applied
Scientific EffectEsterification: Chemical Bonding

Implementation Method 2

performing amidation reaction that converts an esterified form of a sialic acid modified through the esterification into an amidated form through contacting the sample with an amidation reaction solution containing at least one compound selected from the group consisting of ammonia, amines, hydrazine, hydrazine derivatives, and hydroxyamine, and salts thereof

Methodology Applied
Scientific EffectAmidation: Chemical Bonding

Data Source

PatentUS12216113B2Method for preparing analysis sample, analysis method, and kit for preparing analysis sample
Publication Date: 2025.02.04 SHIMADZU CORP
  • US12216113B2 patent drawing
  • US12216113B2 patent drawing
  • US12216113B2 patent drawing

AI summary

A method for preparing an analysis sample from a sample containing a glycan, includes: performing esterification reaction that subjects at least a part of a sialic acid included in the glycan to esterification other than lactonization; and performing amidation reaction that converts an esterified form of a sialic acid modified through the esterification into an amidated form through contacting the sample with an amidation reaction solution containing at least one compound selected from the group consisting of ammonia, amines, hydrazine, hydrazine derivatives, and hydroxyamine, and salts thereof to be reacted with the sialic acid modified through the esterification.