Characterization of 4-deoxy-beta-L-threo-hex-4-enopyranosyluronic acid attached to xylan in pine kraft pulp and pulping liquor by 1H and 13C NMR spectroscopy

Anita Teleman (Corresponding Author), Vesa Harjunpää, Maija Tenkanen, Johanna Buchert, Tiina Hausalo, Torbjörn Drakenberg, Tapani Vuorinen

Research output: Contribution to journalArticleScientificpeer-review

191 Citations (Scopus)

Abstract

A new acidic sidegroup in xylans, from both kraft pulp and pulping liquor, was identified by NMR spectroscopy. Unmodified oligosaccharides from kraft pulp xylan were obtained by enzymatic hydrolysis with xylanase (Trichoderma reesei).
The acidic oligosaccharides were separated from the neutral forms on an anion exchange resin. The new acidic sidegroup was identified as acid (hexenuronic acid) by 1H and 13C NMR spectroscopy. Hexenuronic acid is a β-elimination product of 4-O-methylglucuronic acid and is formed during kraft pulping. HMBC and NOESY experiments showed that hexenuronic acid is attached β-(1 → 2) to xylose. The NOESY data further indicated that hexenuronic acid protrudes from the main xylan chain.
The pKa values for hexenuronic acid (3.03) and 4-O-methylglucuronic acid (3.14) attached (1 → 2) to xylose were determined from pH-dependent chemical shifts.
Original languageEnglish
Pages (from-to)55-71
JournalCarbohydrate Research
Volume272
Issue number1
DOIs
Publication statusPublished - 1995
MoE publication typeA1 Journal article-refereed

Fingerprint

Kraft process
Xylans
Kraft pulp
Nuclear magnetic resonance spectroscopy
Magnetic Resonance Spectroscopy
Xylose
Oligosaccharides
Anion Exchange Resins
Trichoderma
Enzymatic hydrolysis
Chemical shift
Hydrolysis
hexenuronic acid
Proton Magnetic Resonance Spectroscopy
Carbon-13 Magnetic Resonance Spectroscopy
Acids
Experiments

Cite this

Teleman, Anita ; Harjunpää, Vesa ; Tenkanen, Maija ; Buchert, Johanna ; Hausalo, Tiina ; Drakenberg, Torbjörn ; Vuorinen, Tapani. / Characterization of 4-deoxy-beta-L-threo-hex-4-enopyranosyluronic acid attached to xylan in pine kraft pulp and pulping liquor by 1H and 13C NMR spectroscopy. In: Carbohydrate Research. 1995 ; Vol. 272, No. 1. pp. 55-71.
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title = "Characterization of 4-deoxy-beta-L-threo-hex-4-enopyranosyluronic acid attached to xylan in pine kraft pulp and pulping liquor by 1H and 13C NMR spectroscopy",
abstract = "A new acidic sidegroup in xylans, from both kraft pulp and pulping liquor, was identified by NMR spectroscopy. Unmodified oligosaccharides from kraft pulp xylan were obtained by enzymatic hydrolysis with xylanase (Trichoderma reesei). The acidic oligosaccharides were separated from the neutral forms on an anion exchange resin. The new acidic sidegroup was identified as acid (hexenuronic acid) by 1H and 13C NMR spectroscopy. Hexenuronic acid is a β-elimination product of 4-O-methylglucuronic acid and is formed during kraft pulping. HMBC and NOESY experiments showed that hexenuronic acid is attached β-(1 → 2) to xylose. The NOESY data further indicated that hexenuronic acid protrudes from the main xylan chain. The pKa values for hexenuronic acid (3.03) and 4-O-methylglucuronic acid (3.14) attached (1 → 2) to xylose were determined from pH-dependent chemical shifts.",
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Characterization of 4-deoxy-beta-L-threo-hex-4-enopyranosyluronic acid attached to xylan in pine kraft pulp and pulping liquor by 1H and 13C NMR spectroscopy. / Teleman, Anita (Corresponding Author); Harjunpää, Vesa; Tenkanen, Maija; Buchert, Johanna; Hausalo, Tiina; Drakenberg, Torbjörn; Vuorinen, Tapani.

In: Carbohydrate Research, Vol. 272, No. 1, 1995, p. 55-71.

Research output: Contribution to journalArticleScientificpeer-review

TY - JOUR

T1 - Characterization of 4-deoxy-beta-L-threo-hex-4-enopyranosyluronic acid attached to xylan in pine kraft pulp and pulping liquor by 1H and 13C NMR spectroscopy

AU - Teleman, Anita

AU - Harjunpää, Vesa

AU - Tenkanen, Maija

AU - Buchert, Johanna

AU - Hausalo, Tiina

AU - Drakenberg, Torbjörn

AU - Vuorinen, Tapani

N1 - Project code: B5SU00174

PY - 1995

Y1 - 1995

N2 - A new acidic sidegroup in xylans, from both kraft pulp and pulping liquor, was identified by NMR spectroscopy. Unmodified oligosaccharides from kraft pulp xylan were obtained by enzymatic hydrolysis with xylanase (Trichoderma reesei). The acidic oligosaccharides were separated from the neutral forms on an anion exchange resin. The new acidic sidegroup was identified as acid (hexenuronic acid) by 1H and 13C NMR spectroscopy. Hexenuronic acid is a β-elimination product of 4-O-methylglucuronic acid and is formed during kraft pulping. HMBC and NOESY experiments showed that hexenuronic acid is attached β-(1 → 2) to xylose. The NOESY data further indicated that hexenuronic acid protrudes from the main xylan chain. The pKa values for hexenuronic acid (3.03) and 4-O-methylglucuronic acid (3.14) attached (1 → 2) to xylose were determined from pH-dependent chemical shifts.

AB - A new acidic sidegroup in xylans, from both kraft pulp and pulping liquor, was identified by NMR spectroscopy. Unmodified oligosaccharides from kraft pulp xylan were obtained by enzymatic hydrolysis with xylanase (Trichoderma reesei). The acidic oligosaccharides were separated from the neutral forms on an anion exchange resin. The new acidic sidegroup was identified as acid (hexenuronic acid) by 1H and 13C NMR spectroscopy. Hexenuronic acid is a β-elimination product of 4-O-methylglucuronic acid and is formed during kraft pulping. HMBC and NOESY experiments showed that hexenuronic acid is attached β-(1 → 2) to xylose. The NOESY data further indicated that hexenuronic acid protrudes from the main xylan chain. The pKa values for hexenuronic acid (3.03) and 4-O-methylglucuronic acid (3.14) attached (1 → 2) to xylose were determined from pH-dependent chemical shifts.

U2 - 10.1016/0008-6215(95)96873-M

DO - 10.1016/0008-6215(95)96873-M

M3 - Article

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SN - 0008-6215

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