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

M. Almond, P.B. Shaw, P.N. Humphreys, M.J. Chadha, Klaus Niemelä, A.P. Laws (Corresponding Author)

Research output: Contribution to journalArticleScientificpeer-review

6 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 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).
Original languageEnglish
Pages (from-to)51-57
Number of pages6
JournalCarbohydrate Research
Volume363
DOIs
Publication statusPublished - 2012
MoE publication typeA1 Journal article-refereed

Fingerprint

Lactones
Acids
Hydrolysis
Rate constants
Alkalies
Nuclear magnetic resonance
Degradation
Kinetics

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

Cite this

Almond, M. ; Shaw, P.B. ; Humphreys, P.N. ; Chadha, M.J. ; Niemelä, Klaus ; Laws, A.P. / Behaviour of xyloisosaccharinic acid and xyloisosaccharino-1,4-lactone in aqueous solutions at varying pHs. In: Carbohydrate Research. 2012 ; Vol. 363. pp. 51-57.
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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",
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Behaviour of xyloisosaccharinic acid and xyloisosaccharino-1,4-lactone in aqueous solutions at varying pHs. / Almond, M.; Shaw, P.B.; Humphreys, P.N.; Chadha, M.J.; Niemelä, Klaus; Laws, A.P. (Corresponding Author).

In: Carbohydrate Research, Vol. 363, 2012, p. 51-57.

Research output: Contribution to journalArticleScientificpeer-review

TY - JOUR

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

AU - Almond, M.

AU - Shaw, P.B.

AU - Humphreys, P.N.

AU - Chadha, M.J.

AU - Niemelä, Klaus

AU - Laws, A.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

VL - 363

SP - 51

EP - 57

JO - Carbohydrate Research

JF - Carbohydrate Research

SN - 0008-6215

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