Convergent strategy for the synthesis of S-linked oligoxylans

Beatrice Bonora, Irene Boos, Mads Hartvig Clausen

Research output: Contribution to journalJournal articleResearchpeer-review

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Abstract

Arabinoxylans (AX) are a major class of hemicellulose and an important polysaccharide component of lignocellulosic biomass. To utilize the glycan polymer effectively, it is desirable to learn more about the enzymatic hydrolysis of AXs. Well-defined glycans can help to elucidate these processes. Here, we report the efficient synthesis of a mixed O- and S-linked tetraxylan. This thio-oligosaccharide has been developed as a putative inhibitor of arabinoxylan degrading enzymes used for the saccharification of biomass. Two common approaches for the synthesis of thio-oligosaccharides, either involving 1-
thioglycoside donors or thioacceptors, are presented and compared regarding byproduct formation and yields. Both methods have shown to be useful for the synthesis of thiolinkages in oligoxylans assembly. However, the success of the reaction is highly dependent on the “match” between donors and
acceptors.
Original languageEnglish
JournalCarbohydrate Research
Pages (from-to)53-57
ISSN0008-6215
DOIs
Publication statusPublished - 2017

Cite this

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title = "Convergent strategy for the synthesis of S-linked oligoxylans",
abstract = "Arabinoxylans (AX) are a major class of hemicellulose and an important polysaccharide component of lignocellulosic biomass. To utilize the glycan polymer effectively, it is desirable to learn more about the enzymatic hydrolysis of AXs. Well-defined glycans can help to elucidate these processes. Here, we report the efficient synthesis of a mixed O- and S-linked tetraxylan. This thio-oligosaccharide has been developed as a putative inhibitor of arabinoxylan degrading enzymes used for the saccharification of biomass. Two common approaches for the synthesis of thio-oligosaccharides, either involving 1-thioglycoside donors or thioacceptors, are presented and compared regarding byproduct formation and yields. Both methods have shown to be useful for the synthesis of thiolinkages in oligoxylans assembly. However, the success of the reaction is highly dependent on the “match” between donors andacceptors.",
author = "Beatrice Bonora and Irene Boos and Clausen, {Mads Hartvig}",
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Convergent strategy for the synthesis of S-linked oligoxylans. / Bonora, Beatrice; Boos, Irene; Clausen, Mads Hartvig.

In: Carbohydrate Research, 2017, p. 53-57.

Research output: Contribution to journalJournal articleResearchpeer-review

TY - JOUR

T1 - Convergent strategy for the synthesis of S-linked oligoxylans

AU - Bonora, Beatrice

AU - Boos, Irene

AU - Clausen, Mads Hartvig

PY - 2017

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AB - Arabinoxylans (AX) are a major class of hemicellulose and an important polysaccharide component of lignocellulosic biomass. To utilize the glycan polymer effectively, it is desirable to learn more about the enzymatic hydrolysis of AXs. Well-defined glycans can help to elucidate these processes. Here, we report the efficient synthesis of a mixed O- and S-linked tetraxylan. This thio-oligosaccharide has been developed as a putative inhibitor of arabinoxylan degrading enzymes used for the saccharification of biomass. Two common approaches for the synthesis of thio-oligosaccharides, either involving 1-thioglycoside donors or thioacceptors, are presented and compared regarding byproduct formation and yields. Both methods have shown to be useful for the synthesis of thiolinkages in oligoxylans assembly. However, the success of the reaction is highly dependent on the “match” between donors andacceptors.

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DO - 10.1016/j.carres.2017.03.016

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JO - Carbohydrate Research

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