Behaviour of xyloisosaccharinic acid and xyloisosaccharino-1,4-lactone in aqueous solutions at varying pHs

Michael Almond; Paul B. Shaw; Paul N. Humphreys; Marcus J. Chadha; Klaus Niemelä; Andrew P. Laws

doi:10.1016/j.carres.2012.09.019

Behaviour of xyloisosaccharinic acid and xyloisosaccharino-1,4-lactone in aqueous solutions at varying pHs

Michael Almond
, Paul B. Shaw
, Paul N. Humphreys
, Marcus J. Chadha
, Klaus Niemelä
, Andrew P. Laws^*

^*Corresponding author for this work

University of Huddersfield

Research output: Contribution to journal › Article › Scientific › peer-review

8 Citations (Scopus)

Abstract

Xyloisosaccharinic acid is one of the major degradation products formed during the alkali catalysed hydrolysis of hemicelluloses. In acidic solution xyloisosaccharinic acid undergoes an acid catalysed lactonisation to generate xyloisosaccharino-1,4-lactone. We report here the solution phase properties of xyloisosaccharinic including measurement of its aqueous pK_a (3.00 ± 0.05) using ¹³C NMR methods. We also report rate constants for the acid catalysed lactonisation, k_lact(D20), of xyloisosaccharinic acid and the results of our investigations of the kinetics of hydrolysis of xyloisosaccharino-1,4-lactone at acidic and basic pHs. The second-order rate constants for the hydrolysis reactions k_HO– (25 M⁻¹ s⁻¹) and k_D+ (4.13 E-4 M⁻¹ s⁻¹).

Original language	English
Pages (from-to)	51-57
Journal	Carbohydrate Research
Volume	363
DOIs	https://doi.org/10.1016/j.carres.2012.09.019
Publication status	Published - 2012
MoE publication type	A1 Journal article-refereed

Keywords

2,4-Dihydroxy-2-hydroxymethylbutanoic acid
3-Deoxy-2-C-hydroxymethyl-d,l-tetronic acid
PK a measurement
Xyloisosaccharinic acid
Xyloisosaccharino-1,4-lactone

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10.1016/j.carres.2012.09.019

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@article{56fe567ce10f4e1a9957356f05dfd42b,

title = "Behaviour of xyloisosaccharinic acid and xyloisosaccharino-1,4-lactone in aqueous solutions at varying pHs",

abstract = "Xyloisosaccharinic acid is one of the major degradation products formed during the alkali catalysed hydrolysis of hemicelluloses. In acidic solution xyloisosaccharinic acid undergoes an acid catalysed lactonisation to generate xyloisosaccharino-1,4-lactone. We report here the solution phase properties of xyloisosaccharinic including measurement of its aqueous pKa (3.00 ± 0.05) using 13C NMR methods. We also report rate constants for the acid catalysed lactonisation, klact(D20), of xyloisosaccharinic acid and the results of our investigations of the kinetics of hydrolysis of xyloisosaccharino-1,4-lactone at acidic and basic pHs. The second-order rate constants for the hydrolysis reactions kHO– (25 M−1 s−1) and kD+ (4.13 E-4 M−1 s−1).",

keywords = "2,4-Dihydroxy-2-hydroxymethylbutanoic acid, 3-Deoxy-2-C-hydroxymethyl-d,l-tetronic acid, PK a measurement, Xyloisosaccharinic acid, Xyloisosaccharino-1,4-lactone",

author = "Michael Almond and Shaw, \{Paul B.\} and Humphreys, \{Paul N.\} and Chadha, \{Marcus J.\} and Klaus Niemel{\"a} and Laws, \{Andrew P.\}",

year = "2012",

doi = "10.1016/j.carres.2012.09.019",

language = "English",

volume = "363",

pages = "51--57",

journal = "Carbohydrate Research",

issn = "0008-6215",

publisher = "Elsevier",

}

TY - JOUR

T1 - Behaviour of xyloisosaccharinic acid and xyloisosaccharino-1,4-lactone in aqueous solutions at varying pHs

AU - Almond, Michael

AU - Shaw, Paul B.

AU - Humphreys, Paul N.

AU - Chadha, Marcus J.

AU - Niemelä, Klaus

AU - Laws, Andrew P.

PY - 2012

Y1 - 2012

N2 - Xyloisosaccharinic acid is one of the major degradation products formed during the alkali catalysed hydrolysis of hemicelluloses. In acidic solution xyloisosaccharinic acid undergoes an acid catalysed lactonisation to generate xyloisosaccharino-1,4-lactone. We report here the solution phase properties of xyloisosaccharinic including measurement of its aqueous pKa (3.00 ± 0.05) using 13C NMR methods. We also report rate constants for the acid catalysed lactonisation, klact(D20), of xyloisosaccharinic acid and the results of our investigations of the kinetics of hydrolysis of xyloisosaccharino-1,4-lactone at acidic and basic pHs. The second-order rate constants for the hydrolysis reactions kHO– (25 M−1 s−1) and kD+ (4.13 E-4 M−1 s−1).

AB - Xyloisosaccharinic acid is one of the major degradation products formed during the alkali catalysed hydrolysis of hemicelluloses. In acidic solution xyloisosaccharinic acid undergoes an acid catalysed lactonisation to generate xyloisosaccharino-1,4-lactone. We report here the solution phase properties of xyloisosaccharinic including measurement of its aqueous pKa (3.00 ± 0.05) using 13C NMR methods. We also report rate constants for the acid catalysed lactonisation, klact(D20), of xyloisosaccharinic acid and the results of our investigations of the kinetics of hydrolysis of xyloisosaccharino-1,4-lactone at acidic and basic pHs. The second-order rate constants for the hydrolysis reactions kHO– (25 M−1 s−1) and kD+ (4.13 E-4 M−1 s−1).

KW - 2,4-Dihydroxy-2-hydroxymethylbutanoic acid

KW - 3-Deoxy-2-C-hydroxymethyl-d,l-tetronic acid

KW - PK a measurement

KW - Xyloisosaccharinic acid

KW - Xyloisosaccharino-1,4-lactone

U2 - 10.1016/j.carres.2012.09.019

DO - 10.1016/j.carres.2012.09.019

M3 - Article

SN - 0008-6215

VL - 363

SP - 51

EP - 57

JO - Carbohydrate Research

JF - Carbohydrate Research

ER -

Behaviour of xyloisosaccharinic acid and xyloisosaccharino-1,4-lactone in aqueous solutions at varying pHs

Abstract

Keywords

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