Identification of the acidic degradation products of hexenuronic acid and characterisation of hexenuronic acid-substituted xylooligosaccharides by NMR spectroscopy

Anita Teleman (Corresponding Author), Tiina Hausalo, Maija Tenkanen, Tapani Vuorinen

Research output: Contribution to journalArticleScientificpeer-review

92 Citations (Scopus)

Abstract

A 4-O-methylglucuronoxylan was converted into a hexenuronoxylan at high temperature and alkalinity similar to the conditions used during kraft pulping. The hexenuronoxylan was hydrolysed with enzymes, and acidic xylooligosaccharides were separated from the hydrolysate by anion-exchange and size-exclusion chromatography. The primary structure of the two main hexenuronic acid-substituted xylooligosaccharides (a tetramer and a pentamer) was determined by two-dimensional 1H and 13C NMR spectroscopy. The 4-deoxy-hexenutronic acid is not stable under the acid hydrolysis step of conventional carbohydrate analysis. Here, we have identified the acidic degradation products of 4-deoxy-hexenuronic acid by NMR spectroscopy. Two degradation pathways were observed, both resulting in a furan derivative.
Original languageEnglish
Pages (from-to)197-208
Number of pages12
JournalCarbohydrate Research
Volume280
Issue number2
DOIs
Publication statusPublished - 1996
MoE publication typeA1 Journal article-refereed

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Nuclear magnetic resonance spectroscopy
Magnetic Resonance Spectroscopy
Kraft process
Degradation
Acids
Size exclusion chromatography
Alkalinity
Gel Chromatography
Anions
Hydrolysis
Carbohydrates
Derivatives
Temperature
Enzymes
hexenuronic acid
xylooligosaccharide
4-O-methyl glucuronoxylan
furan
Carbon-13 Magnetic Resonance Spectroscopy
Proton Magnetic Resonance Spectroscopy

Cite this

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title = "Identification of the acidic degradation products of hexenuronic acid and characterisation of hexenuronic acid-substituted xylooligosaccharides by NMR spectroscopy",
abstract = "A 4-O-methylglucuronoxylan was converted into a hexenuronoxylan at high temperature and alkalinity similar to the conditions used during kraft pulping. The hexenuronoxylan was hydrolysed with enzymes, and acidic xylooligosaccharides were separated from the hydrolysate by anion-exchange and size-exclusion chromatography. The primary structure of the two main hexenuronic acid-substituted xylooligosaccharides (a tetramer and a pentamer) was determined by two-dimensional 1H and 13C NMR spectroscopy. The 4-deoxy-hexenutronic acid is not stable under the acid hydrolysis step of conventional carbohydrate analysis. Here, we have identified the acidic degradation products of 4-deoxy-hexenuronic acid by NMR spectroscopy. Two degradation pathways were observed, both resulting in a furan derivative.",
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Identification of the acidic degradation products of hexenuronic acid and characterisation of hexenuronic acid-substituted xylooligosaccharides by NMR spectroscopy. / Teleman, Anita (Corresponding Author); Hausalo, Tiina; Tenkanen, Maija; Vuorinen, Tapani.

In: Carbohydrate Research, Vol. 280, No. 2, 1996, p. 197-208.

Research output: Contribution to journalArticleScientificpeer-review

TY - JOUR

T1 - Identification of the acidic degradation products of hexenuronic acid and characterisation of hexenuronic acid-substituted xylooligosaccharides by NMR spectroscopy

AU - Teleman, Anita

AU - Hausalo, Tiina

AU - Tenkanen, Maija

AU - Vuorinen, Tapani

PY - 1996

Y1 - 1996

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AB - A 4-O-methylglucuronoxylan was converted into a hexenuronoxylan at high temperature and alkalinity similar to the conditions used during kraft pulping. The hexenuronoxylan was hydrolysed with enzymes, and acidic xylooligosaccharides were separated from the hydrolysate by anion-exchange and size-exclusion chromatography. The primary structure of the two main hexenuronic acid-substituted xylooligosaccharides (a tetramer and a pentamer) was determined by two-dimensional 1H and 13C NMR spectroscopy. The 4-deoxy-hexenutronic acid is not stable under the acid hydrolysis step of conventional carbohydrate analysis. Here, we have identified the acidic degradation products of 4-deoxy-hexenuronic acid by NMR spectroscopy. Two degradation pathways were observed, both resulting in a furan derivative.

U2 - 10.1016/0008-6215(95)00309-6

DO - 10.1016/0008-6215(95)00309-6

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JO - Carbohydrate Research

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