Title: Methods for detecting and determining levels of monolignol ester conjugates incorporated into lignin and compounds relating thereto

Abstract

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.

Inventors:

Ralph, John; Karlen, Steven D.; Lu, Fachuang; Padmakshan, Dharshana

Issue Date:

Tue Aug 16 00:00:00 EDT 2022

Research Org.:

Univ. of Wisconsin, Madison, WI (United States)

Sponsoring Org.:

USDOE

OSTI Identifier:

1924983

Patent Number(s):

11414372

Application Number:

16/252,915

Assignee:

Wisconsin Alumni Research Foundation (Madison, WI)

Patent Classifications (CPCs):

C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07B - GENERAL METHODS OF ORGANIC CHEMISTRY

C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07C - ACYCLIC OR CARBOCYCLIC COMPOUNDS

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C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07B - GENERAL METHODS OF ORGANIC CHEMISTRY

C07B2200/05 - Isotopically modified compounds, e.g. labelled

C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07C - ACYCLIC OR CARBOCYCLIC COMPOUNDS

C07C69/007 - Esters of unsaturated alcohols having the esterified hydroxy group bound to an acyclic carbon atom
C07C69/16 - of dihydroxylic compounds
C07C69/73 - of unsaturated acids
C07C69/732 - of unsaturated hydroxy carboxylic acids
C07C69/734 - Ethers
C07C69/84 - of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring
C07C69/86 - with esterified hydroxyl groups
C07C69/92 - with etherified hydroxyl groups

G - PHYSICS G01 - MEASURING G01N - INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES

G01N2400/26 - Cellulose
G01N2458/15 - Non-radioactive isotope labels, e.g. for detection by mass spectrometry
G01N2560/00 - Chemical aspects of mass spectrometric analysis of biological material
G01N33/50 - Chemical analysis of biological material, e.g. blood, urine

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DOE Contract Number:  

FC02-07ER64494

Resource Type:

Patent

Resource Relation:

Patent File Date: 01/21/2019

Country of Publication:

United States

Language:

English

Subject:

59 BASIC BIOLOGICAL SCIENCES; 09 BIOMASS FUELS