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

Anita Teleman; Vesa Harjunpää; Maija Tenkanen; Johanna Buchert; Tiina Hausalo; Torbjörn Drakenberg; Tapani Vuorinen

doi:10.1016/0008-6215(95)96873-M

Characterization of 4-deoxy-β-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

VTT Technical Research Centre of Finland

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

203 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 4-deoxy-β-l-threo-hex-4-enopyranosyluronic 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 pK_a 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 language	English
Pages (from-to)	55-71
Journal	Carbohydrate Research
Volume	272
Issue number	1
DOIs	https://doi.org/10.1016/0008-6215(95)96873-M
Publication status	Published - 1995
MoE publication type	A1 Journal article-refereed

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10.1016/0008-6215(95)96873-M

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@article{007d74d7ad5c49c8830e82ca76dc9f87,

title = "Characterization of 4-deoxy-β-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 4-deoxy-β-l-threo-hex-4-enopyranosyluronic 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.",

author = "Anita Teleman and Vesa Harjunp{\"a}{\"a} and Maija Tenkanen and Johanna Buchert and Tiina Hausalo and Torbj{\"o}rn Drakenberg and Tapani Vuorinen",

note = "Project code: B5SU00174",

year = "1995",

doi = "10.1016/0008-6215(95)96873-M",

language = "English",

volume = "272",

pages = "55--71",

journal = "Carbohydrate Research",

issn = "0008-6215",

publisher = "Elsevier",

number = "1",

}

Characterization of 4-deoxy-β-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 et al.
In: Carbohydrate Research, Vol. 272, No. 1, 1995, p. 55-71.

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

TY - JOUR

T1 - Characterization of 4-deoxy-β-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 4-deoxy-β-l-threo-hex-4-enopyranosyluronic 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 4-deoxy-β-l-threo-hex-4-enopyranosyluronic 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

SN - 0008-6215

VL - 272

SP - 55

EP - 71

JO - Carbohydrate Research

JF - Carbohydrate Research

IS - 1

ER -

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

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