A robust method for the synthesis and isolation of β-gluco-isosaccharinic acid ((2R,4S)-2,4,5-trihydroxy-2-(hydroxymethyl)pentanoic acid) from cellulose and measurement of its aqueous pKa

Paul B. Shaw, Glenn F. Robinson, Craig R. Rice, Paul N. Humphreys, Andrew P. Laws

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

In alkaline pulping wood pulp is reacted with concentrated aqueous alkali at elevated temperatures. In addition to producing cellulose for the manufacture of paper, alkaline pulping also generates large amounts of isosaccharinic acids as waste products. Isosaccharinic acids are potentially useful raw materials: they are good metal chelating agents and, in their enantiomerically pure form, they are valuable carbon skeletons with predefined stereochemistry that can be easily functionalised for use in synthesis. Despite this, there is no simple procedure for isolating pure beta-(gluco)isosaccharinic acid and very limited work has been undertaken to determine the chemical and physical properties of this compound. We report here a very simple but effective method for the synthesis of a mixture containing equal portions of the two isosaccharinic acids ((2S,4S)-2,4,5-trihydroxy-2-(hydroxymethyl)pentanoic acid and (2R,4S)-2,4,5-trihydroxy-2-(hydroxymethyl)pentanoic acid) and the separation of the two as their tribenzoate esters. We also report for the first time the aqueous pKa of beta-(gluco)isosaccharinic acid (3.61).

Original languageEnglish
Pages (from-to)6-11
Number of pages6
JournalCarbohydrate Research
Volume349
DOIs
Publication statusPublished - 15 Feb 2012

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Pentanoic Acids
Cellulose
Waste Products
Stereochemistry
Alkalies
Chelating Agents
Skeleton
Chemical properties
Pulp
Wood
Raw materials
Esters
Carbon
Physical properties
isosaccharinic acid
Temperature

Cite this

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title = "A robust method for the synthesis and isolation of β-gluco-isosaccharinic acid ((2R,4S)-2,4,5-trihydroxy-2-(hydroxymethyl)pentanoic acid) from cellulose and measurement of its aqueous pKa",
abstract = "In alkaline pulping wood pulp is reacted with concentrated aqueous alkali at elevated temperatures. In addition to producing cellulose for the manufacture of paper, alkaline pulping also generates large amounts of isosaccharinic acids as waste products. Isosaccharinic acids are potentially useful raw materials: they are good metal chelating agents and, in their enantiomerically pure form, they are valuable carbon skeletons with predefined stereochemistry that can be easily functionalised for use in synthesis. Despite this, there is no simple procedure for isolating pure beta-(gluco)isosaccharinic acid and very limited work has been undertaken to determine the chemical and physical properties of this compound. We report here a very simple but effective method for the synthesis of a mixture containing equal portions of the two isosaccharinic acids ((2S,4S)-2,4,5-trihydroxy-2-(hydroxymethyl)pentanoic acid and (2R,4S)-2,4,5-trihydroxy-2-(hydroxymethyl)pentanoic acid) and the separation of the two as their tribenzoate esters. We also report for the first time the aqueous pKa of beta-(gluco)isosaccharinic acid (3.61).",
keywords = "3-Deoxy-2-C-hydroxymethyl-d-pentonic acid, Beta-isosaccharinic acid, Cellulose, Glucoisosaccharinic acid, Isosaccharinic acid",
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TY - JOUR

T1 - A robust method for the synthesis and isolation of β-gluco-isosaccharinic acid ((2R,4S)-2,4,5-trihydroxy-2-(hydroxymethyl)pentanoic acid) from cellulose and measurement of its aqueous pKa

AU - Shaw, Paul B.

AU - Robinson, Glenn F.

AU - Rice, Craig R.

AU - Humphreys, Paul N.

AU - Laws, Andrew P.

PY - 2012/2/15

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N2 - In alkaline pulping wood pulp is reacted with concentrated aqueous alkali at elevated temperatures. In addition to producing cellulose for the manufacture of paper, alkaline pulping also generates large amounts of isosaccharinic acids as waste products. Isosaccharinic acids are potentially useful raw materials: they are good metal chelating agents and, in their enantiomerically pure form, they are valuable carbon skeletons with predefined stereochemistry that can be easily functionalised for use in synthesis. Despite this, there is no simple procedure for isolating pure beta-(gluco)isosaccharinic acid and very limited work has been undertaken to determine the chemical and physical properties of this compound. We report here a very simple but effective method for the synthesis of a mixture containing equal portions of the two isosaccharinic acids ((2S,4S)-2,4,5-trihydroxy-2-(hydroxymethyl)pentanoic acid and (2R,4S)-2,4,5-trihydroxy-2-(hydroxymethyl)pentanoic acid) and the separation of the two as their tribenzoate esters. We also report for the first time the aqueous pKa of beta-(gluco)isosaccharinic acid (3.61).

AB - In alkaline pulping wood pulp is reacted with concentrated aqueous alkali at elevated temperatures. In addition to producing cellulose for the manufacture of paper, alkaline pulping also generates large amounts of isosaccharinic acids as waste products. Isosaccharinic acids are potentially useful raw materials: they are good metal chelating agents and, in their enantiomerically pure form, they are valuable carbon skeletons with predefined stereochemistry that can be easily functionalised for use in synthesis. Despite this, there is no simple procedure for isolating pure beta-(gluco)isosaccharinic acid and very limited work has been undertaken to determine the chemical and physical properties of this compound. We report here a very simple but effective method for the synthesis of a mixture containing equal portions of the two isosaccharinic acids ((2S,4S)-2,4,5-trihydroxy-2-(hydroxymethyl)pentanoic acid and (2R,4S)-2,4,5-trihydroxy-2-(hydroxymethyl)pentanoic acid) and the separation of the two as their tribenzoate esters. We also report for the first time the aqueous pKa of beta-(gluco)isosaccharinic acid (3.61).

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