Synthesis of glycoconjugates utilizing the regioselectivity of a lytic polysaccharide monooxygenase

Research output: Contribution to journal › Journal article › Research › peer-review

Standard

Synthesis of glycoconjugates utilizing the regioselectivity of a lytic polysaccharide monooxygenase. / Westereng, Bjørge; Kracun, Stjepan K.; Leivers, Shaun; Arntzen, Magnus O.; Aachmann, Finn L.; Eijsink, Vincent G. H.

In: Scientific Reports, Vol. 10, No. 1, 13197, 2020.

Research output: Contribution to journal › Journal article › Research › peer-review

Harvard

Westereng, B, Kracun, SK, Leivers, S, Arntzen, MO, Aachmann, FL & Eijsink, VGH 2020, 'Synthesis of glycoconjugates utilizing the regioselectivity of a lytic polysaccharide monooxygenase', Scientific Reports, vol. 10, no. 1, 13197. https://doi.org/10.1038/s41598-020-69951-7

APA

Westereng, B., Kracun, S. K., Leivers, S., Arntzen, M. O., Aachmann, F. L., & Eijsink, V. G. H. (2020). Synthesis of glycoconjugates utilizing the regioselectivity of a lytic polysaccharide monooxygenase. Scientific Reports, 10(1), [13197]. https://doi.org/10.1038/s41598-020-69951-7

Vancouver

Westereng B, Kracun SK, Leivers S, Arntzen MO, Aachmann FL, Eijsink VGH. Synthesis of glycoconjugates utilizing the regioselectivity of a lytic polysaccharide monooxygenase. Scientific Reports. 2020;10(1). 13197. https://doi.org/10.1038/s41598-020-69951-7

Author

Westereng, Bjørge ; Kracun, Stjepan K. ; Leivers, Shaun ; Arntzen, Magnus O. ; Aachmann, Finn L. ; Eijsink, Vincent G. H. / Synthesis of glycoconjugates utilizing the regioselectivity of a lytic polysaccharide monooxygenase. In: Scientific Reports. 2020 ; Vol. 10, No. 1.

Bibtex

@article{8bcd4de4f4dd4a40897bc932fc4b38fd,
title = "Synthesis of glycoconjugates utilizing the regioselectivity of a lytic polysaccharide monooxygenase",
abstract = "Polysaccharides from plant biomass are the most abundant renewable chemicals on Earth and can potentially be converted to a wide variety of useful glycoconjugates. Potential applications of glycoconjugates include therapeutics and drug delivery, vaccine development and as fine chemicals. While anomeric hydroxyl groups of carbohydrates are amenable to a variety of useful chemical modifications, selective cross-coupling to non-reducing ends has remained challenging. Several lytic polysaccharide monooxygenases (LPMOs), powerful enzymes known for their application in cellulose degradation, specifically oxidize non-reducing ends, introducing carbonyl groups that can be utilized for chemical coupling. This study provides a simple and highly specific approach to produce oxime-based glycoconjugates from LPMO-functionalized oligosaccharides. The products are evaluated by HPLC, mass spectrometry and NMR. Furthermore, we demonstrate potential biodegradability of these glycoconjugates using selective enzymes.",
keywords = "PYRANOSE DEHYDROGENASE, AGARICUS-MELEAGRIS, CELLULOSE, OLIGOSACCHARIDES, OXIDATION, HOMOGALACTURONAN, DEGRADATION, CONVERSION, PRODUCTS, CLEAVAGE",
author = "Bj{\o}rge Westereng and Kracun, {Stjepan K.} and Shaun Leivers and Arntzen, {Magnus O.} and Aachmann, {Finn L.} and Eijsink, {Vincent G. H.}",
year = "2020",
doi = "10.1038/s41598-020-69951-7",
language = "English",
volume = "10",
journal = "Scientific Reports",
issn = "2045-2322",
publisher = "nature publishing group",
number = "1",

}

RIS

TY - JOUR

T1 - Synthesis of glycoconjugates utilizing the regioselectivity of a lytic polysaccharide monooxygenase

AU - Westereng, Bjørge

AU - Kracun, Stjepan K.

AU - Leivers, Shaun

AU - Arntzen, Magnus O.

AU - Aachmann, Finn L.

AU - Eijsink, Vincent G. H.

PY - 2020

Y1 - 2020

N2 - Polysaccharides from plant biomass are the most abundant renewable chemicals on Earth and can potentially be converted to a wide variety of useful glycoconjugates. Potential applications of glycoconjugates include therapeutics and drug delivery, vaccine development and as fine chemicals. While anomeric hydroxyl groups of carbohydrates are amenable to a variety of useful chemical modifications, selective cross-coupling to non-reducing ends has remained challenging. Several lytic polysaccharide monooxygenases (LPMOs), powerful enzymes known for their application in cellulose degradation, specifically oxidize non-reducing ends, introducing carbonyl groups that can be utilized for chemical coupling. This study provides a simple and highly specific approach to produce oxime-based glycoconjugates from LPMO-functionalized oligosaccharides. The products are evaluated by HPLC, mass spectrometry and NMR. Furthermore, we demonstrate potential biodegradability of these glycoconjugates using selective enzymes.

AB - Polysaccharides from plant biomass are the most abundant renewable chemicals on Earth and can potentially be converted to a wide variety of useful glycoconjugates. Potential applications of glycoconjugates include therapeutics and drug delivery, vaccine development and as fine chemicals. While anomeric hydroxyl groups of carbohydrates are amenable to a variety of useful chemical modifications, selective cross-coupling to non-reducing ends has remained challenging. Several lytic polysaccharide monooxygenases (LPMOs), powerful enzymes known for their application in cellulose degradation, specifically oxidize non-reducing ends, introducing carbonyl groups that can be utilized for chemical coupling. This study provides a simple and highly specific approach to produce oxime-based glycoconjugates from LPMO-functionalized oligosaccharides. The products are evaluated by HPLC, mass spectrometry and NMR. Furthermore, we demonstrate potential biodegradability of these glycoconjugates using selective enzymes.

KW - PYRANOSE DEHYDROGENASE

KW - AGARICUS-MELEAGRIS

KW - CELLULOSE

KW - OLIGOSACCHARIDES

KW - OXIDATION

KW - HOMOGALACTURONAN

KW - DEGRADATION

KW - CONVERSION

KW - PRODUCTS

KW - CLEAVAGE

U2 - 10.1038/s41598-020-69951-7

DO - 10.1038/s41598-020-69951-7

M3 - Journal article

C2 - 32764705

VL - 10

JO - Scientific Reports

JF - Scientific Reports

SN - 2045-2322

IS - 1

M1 - 13197

ER -

ID: 249866164