Biopolymer Modification in Organic Fluorine Solvents

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Solution Overview

Problem

Current methods for chemically modifying biopolymers and polypeptides, such as collagen and gelatin, face challenges with introducing hydrophobic compounds and those that degrade under basic conditions, as they require high solubility in water and are limited by reaction conditions.

Innovation Solution

Chemical modification of biopolymers and polypeptides is achieved in a reaction solution containing an organic fluorine compound, specifically using compounds like 2,2,2-trifluoroethanol, which allows for efficient introduction of functional groups, including hydrophobic and alkali-sensitive compounds, using condensing agents like carbodiimide and epoxides.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Adaptability or versatility

If chemical modification is performed in water system using condensing agent, then water soluble biopolymer can be modified, but poorly soluble compound cannot be introduced

Engineering Contradiction:
Improverange of introducable functional groupsVSAvoidsolubility of compound
Core Design Contradiction:
Adaptability or versatilityVSQuantity of substance

Solution Approach 1:

The invention changes the solvent parameter from water to organic fluorine compound (such as HFIP, TFE, or CF3COOH), enabling dissolution and reaction of poorly soluble hydrophobic compounds while maintaining biopolymer solubility and reactivity

Inventive Principle:
Principle #35Parameter changes

2Quantity of substance

If compound is dissolved in sodium hydroxide solution to improve solubility, then reaction can proceed, but compound with functional group causing degradation or reaction in alkaline state cannot be used

Engineering Contradiction:
Improvesolubility of compoundVSAvoidstability of functional group
Core Design Contradiction:
Quantity of substanceVSReliability

Solution Approach 1:

The invention changes the pH parameter by using organic fluorine compounds as solvents, creating a non-alkaline reaction environment that prevents degradation of alkali-sensitive functional groups while maintaining adequate solubility through the fluorinated solvent's unique properties

Inventive Principle:
Principle #35Parameter changes

3Adaptability or versatility

If highly hydrophobic compound is used, then new functional properties can be introduced, but solubility in water system is insufficient

Engineering Contradiction:
Improvefunctional properties of biopolymerVSAvoidsolubility of compound
Core Design Contradiction:
Adaptability or versatilityVSQuantity of substance

Solution Approach 1:

The invention changes the solvent's hydrophobicity parameter by using organic fluorine compounds, which have unique solvation properties that can dissolve both hydrophobic compounds and maintain biopolymer solubility, enabling introduction of highly hydrophobic functional groups

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The organic fluorine compound acts as an intermediary solvent that mediates between the hydrophobic compound and the biopolymer, enabling their interaction in a single phase system without requiring emulsifiers or co-solvents

Inventive Principle:
Principle #24Intermediary (Mediator)

4Ease of manufacture

If gelatin is used as substrate, then chemical modification can be performed, but gel formation at low temperature in aqueous solution complicates handling

Engineering Contradiction:
Improvechemical modifiabilityVSAvoidhandling of substrate
Core Design Contradiction:
Ease of manufactureVSEase of operation

Solution Approach 1:

The invention changes the temperature parameter by conducting the reaction at low temperature (0-25°C) in organic fluorine compound solvent, where gelatin remains soluble and does not form gel, enabling easy handling during reaction while maintaining chemical modifiability

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 enables more efficient reactions, easy handling of reactive substrates, and the ability to introduce various functional groups, leading to highly functionalized biopolymers and polypeptides with improved properties.

Implementation Method 1

a biopolymer or polypeptide is chemically modified in a reaction solution containing an organic fluorine compound

Methodology Applied
Scientific EffectSolvation: Solvation

Implementation Method 2

water soluble biopolymer or polypeptide is dissolved in water, and is reacted with a compound having a desired functional group by a condensing agent

Methodology Applied
Scientific EffectCondensation reaction: Chemical Bonding

Data Source

PatentEP2221334B1Method for chemically modifying biopolymer and polypeptide
Publication Date: 2016.12.28 FUJIFILM CORP

AI summary

It is an object of the present invention to provide a method for chemically modifying biopolymer and polypeptide with a hydrophobic compound or a compound which causes degradation or reaction under basic condition. The present invention provides a method for producing a chemically modified biopolymer or polypeptide, wherein a biopolymer or polypeptide is chemically modified in a reaction solution containing an organic fluorine compound.