Lactose- and cellobiose-derived branched trisaccharides and a sucrose-containing trisaccharide produced by acceptor reactions of Weissella confusa dextransucrase

Qiao Shi (Corresponding Author), Minna Juvonen, Yaxi Hou, Ilkka Kajala, Antti Nyyssölä, Ndegwa Henry Maina, Hannu Maaheimo, Liisa Virkki, Maija Tenkanen

Research output: Contribution to journalArticleScientificpeer-review

13 Citations (Scopus)

Abstract

Dextran-producing Weissella have received significant attention. However, except for maltose, the acceptor reactions of Weissella dextransucrases with different sugars have not been investigated. The action of recombinant Weissella confusa VTT E-90392 dextransucrase was tested with several potential acceptors, particularly, analogs lactose and cellobiose. The major acceptor products of both disaccharides were identified as branched trisaccharides, with a glucosyl residue [alpha]-(1->2)-linked to the acceptor's reducing end. An additional product, isomelezitose (6Fru-[alpha]-Glcp-sucrose), was also produced when using lactose as an acceptor. This is the first report of the synthesis of isomelezitose by a dextransucrase. The NMR spectra of the three trisaccharides were fully assigned, and their structures were confirmed by selective enzymatic hydrolysis. The trisaccharides prepared from 13C6glc sucrose and lactose were analyzed by ESI-MSn, and the fragmentation patterns of these compounds were characterized.
Original languageEnglish
Pages (from-to)226-236
JournalFood Chemistry
Volume190
DOIs
Publication statusPublished - 2016
MoE publication typeA1 Journal article-refereed

Fingerprint

dextransucrase
Weissella
Weissella confusa
trisaccharides
Trisaccharides
Cellobiose
cellobiose
Lactose
lactose
Sucrose
sucrose
Enzymatic hydrolysis
Maltose
Disaccharides
disaccharides
dextran
enzymatic hydrolysis
maltose
Dextrans
Sugars

Keywords

  • Dextransucrase
  • Oligosaccharide
  • Weissella
  • Isomelezitose
  • Tandem mass spectrometry
  • NMR

Cite this

Shi, Qiao ; Juvonen, Minna ; Hou, Yaxi ; Kajala, Ilkka ; Nyyssölä, Antti ; Maina, Ndegwa Henry ; Maaheimo, Hannu ; Virkki, Liisa ; Tenkanen, Maija. / Lactose- and cellobiose-derived branched trisaccharides and a sucrose-containing trisaccharide produced by acceptor reactions of Weissella confusa dextransucrase. In: Food Chemistry. 2016 ; Vol. 190. pp. 226-236.
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abstract = "Dextran-producing Weissella have received significant attention. However, except for maltose, the acceptor reactions of Weissella dextransucrases with different sugars have not been investigated. The action of recombinant Weissella confusa VTT E-90392 dextransucrase was tested with several potential acceptors, particularly, analogs lactose and cellobiose. The major acceptor products of both disaccharides were identified as branched trisaccharides, with a glucosyl residue [alpha]-(1->2)-linked to the acceptor's reducing end. An additional product, isomelezitose (6Fru-[alpha]-Glcp-sucrose), was also produced when using lactose as an acceptor. This is the first report of the synthesis of isomelezitose by a dextransucrase. The NMR spectra of the three trisaccharides were fully assigned, and their structures were confirmed by selective enzymatic hydrolysis. The trisaccharides prepared from 13C6glc sucrose and lactose were analyzed by ESI-MSn, and the fragmentation patterns of these compounds were characterized.",
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author = "Qiao Shi and Minna Juvonen and Yaxi Hou and Ilkka Kajala and Antti Nyyss{\"o}l{\"a} and Maina, {Ndegwa Henry} and Hannu Maaheimo and Liisa Virkki and Maija Tenkanen",
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Lactose- and cellobiose-derived branched trisaccharides and a sucrose-containing trisaccharide produced by acceptor reactions of Weissella confusa dextransucrase. / Shi, Qiao (Corresponding Author); Juvonen, Minna; Hou, Yaxi; Kajala, Ilkka; Nyyssölä, Antti; Maina, Ndegwa Henry; Maaheimo, Hannu; Virkki, Liisa; Tenkanen, Maija.

In: Food Chemistry, Vol. 190, 2016, p. 226-236.

Research output: Contribution to journalArticleScientificpeer-review

TY - JOUR

T1 - Lactose- and cellobiose-derived branched trisaccharides and a sucrose-containing trisaccharide produced by acceptor reactions of Weissella confusa dextransucrase

AU - Shi, Qiao

AU - Juvonen, Minna

AU - Hou, Yaxi

AU - Kajala, Ilkka

AU - Nyyssölä, Antti

AU - Maina, Ndegwa Henry

AU - Maaheimo, Hannu

AU - Virkki, Liisa

AU - Tenkanen, Maija

PY - 2016

Y1 - 2016

N2 - Dextran-producing Weissella have received significant attention. However, except for maltose, the acceptor reactions of Weissella dextransucrases with different sugars have not been investigated. The action of recombinant Weissella confusa VTT E-90392 dextransucrase was tested with several potential acceptors, particularly, analogs lactose and cellobiose. The major acceptor products of both disaccharides were identified as branched trisaccharides, with a glucosyl residue [alpha]-(1->2)-linked to the acceptor's reducing end. An additional product, isomelezitose (6Fru-[alpha]-Glcp-sucrose), was also produced when using lactose as an acceptor. This is the first report of the synthesis of isomelezitose by a dextransucrase. The NMR spectra of the three trisaccharides were fully assigned, and their structures were confirmed by selective enzymatic hydrolysis. The trisaccharides prepared from 13C6glc sucrose and lactose were analyzed by ESI-MSn, and the fragmentation patterns of these compounds were characterized.

AB - Dextran-producing Weissella have received significant attention. However, except for maltose, the acceptor reactions of Weissella dextransucrases with different sugars have not been investigated. The action of recombinant Weissella confusa VTT E-90392 dextransucrase was tested with several potential acceptors, particularly, analogs lactose and cellobiose. The major acceptor products of both disaccharides were identified as branched trisaccharides, with a glucosyl residue [alpha]-(1->2)-linked to the acceptor's reducing end. An additional product, isomelezitose (6Fru-[alpha]-Glcp-sucrose), was also produced when using lactose as an acceptor. This is the first report of the synthesis of isomelezitose by a dextransucrase. The NMR spectra of the three trisaccharides were fully assigned, and their structures were confirmed by selective enzymatic hydrolysis. The trisaccharides prepared from 13C6glc sucrose and lactose were analyzed by ESI-MSn, and the fragmentation patterns of these compounds were characterized.

KW - Dextransucrase

KW - Oligosaccharide

KW - Weissella

KW - Isomelezitose

KW - Tandem mass spectrometry

KW - NMR

U2 - 10.1016/j.foodchem.2015.05.090

DO - 10.1016/j.foodchem.2015.05.090

M3 - Article

VL - 190

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JO - Food Chemistry

JF - Food Chemistry

SN - 0308-8146

ER -