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Chemoenzymatic Synthesis of Asymmetrically Branched Human Milk Oligosaccharide Lacto-N-Hexaose

We herein reported the first chemoenzymatic synthesis of lacto-N-hexaose (LNH) by combining chemical carbohydrate synthesis with a selectively enzymatic glycosylation strategy. A tetrasaccharide core structure GlcNH(2)β1→3 (GlcNAcβ1→6) Galβ1→4Glc, a key precursor for subsequent enzymatic glycan exte...

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Autores principales: Ooi, Kai-Eng, Zhang, Xiu-Wen, Kuo, Cheng-Yu, Liu, Ying-Jia, Yu, Ching-Ching
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Frontiers Media S.A. 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9194828/
https://www.ncbi.nlm.nih.gov/pubmed/35711960
http://dx.doi.org/10.3389/fchem.2022.905105
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author Ooi, Kai-Eng
Zhang, Xiu-Wen
Kuo, Cheng-Yu
Liu, Ying-Jia
Yu, Ching-Ching
author_facet Ooi, Kai-Eng
Zhang, Xiu-Wen
Kuo, Cheng-Yu
Liu, Ying-Jia
Yu, Ching-Ching
author_sort Ooi, Kai-Eng
collection PubMed
description We herein reported the first chemoenzymatic synthesis of lacto-N-hexaose (LNH) by combining chemical carbohydrate synthesis with a selectively enzymatic glycosylation strategy. A tetrasaccharide core structure GlcNH(2)β1→3 (GlcNAcβ1→6) Galβ1→4Glc, a key precursor for subsequent enzymatic glycan extension toward asymmetrically branched human milk oligosaccharides, was synthesized in this work. When the order of galactosyltransferase-catalyzed reactions was appropriately arranged, the β1,4-galactosyl and β1,3-galactosyl moieties could be sequentially assembled on the C6-arm and C3-arm of the tetrasaccharide, respectively, to achieve an efficient LNH synthesis. Lacto-N-neotetraose (LNnH), another common human milk oligosaccharide, was also synthesized en route to the target LNH.
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spelling pubmed-91948282022-06-15 Chemoenzymatic Synthesis of Asymmetrically Branched Human Milk Oligosaccharide Lacto-N-Hexaose Ooi, Kai-Eng Zhang, Xiu-Wen Kuo, Cheng-Yu Liu, Ying-Jia Yu, Ching-Ching Front Chem Chemistry We herein reported the first chemoenzymatic synthesis of lacto-N-hexaose (LNH) by combining chemical carbohydrate synthesis with a selectively enzymatic glycosylation strategy. A tetrasaccharide core structure GlcNH(2)β1→3 (GlcNAcβ1→6) Galβ1→4Glc, a key precursor for subsequent enzymatic glycan extension toward asymmetrically branched human milk oligosaccharides, was synthesized in this work. When the order of galactosyltransferase-catalyzed reactions was appropriately arranged, the β1,4-galactosyl and β1,3-galactosyl moieties could be sequentially assembled on the C6-arm and C3-arm of the tetrasaccharide, respectively, to achieve an efficient LNH synthesis. Lacto-N-neotetraose (LNnH), another common human milk oligosaccharide, was also synthesized en route to the target LNH. Frontiers Media S.A. 2022-05-31 /pmc/articles/PMC9194828/ /pubmed/35711960 http://dx.doi.org/10.3389/fchem.2022.905105 Text en Copyright © 2022 Ooi, Zhang, Kuo, Liu and Yu. https://creativecommons.org/licenses/by/4.0/This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY). The use, distribution or reproduction in other forums is permitted, provided the original author(s) and the copyright owner(s) are credited and that the original publication in this journal is cited, in accordance with accepted academic practice. No use, distribution or reproduction is permitted which does not comply with these terms.
spellingShingle Chemistry
Ooi, Kai-Eng
Zhang, Xiu-Wen
Kuo, Cheng-Yu
Liu, Ying-Jia
Yu, Ching-Ching
Chemoenzymatic Synthesis of Asymmetrically Branched Human Milk Oligosaccharide Lacto-N-Hexaose
title Chemoenzymatic Synthesis of Asymmetrically Branched Human Milk Oligosaccharide Lacto-N-Hexaose
title_full Chemoenzymatic Synthesis of Asymmetrically Branched Human Milk Oligosaccharide Lacto-N-Hexaose
title_fullStr Chemoenzymatic Synthesis of Asymmetrically Branched Human Milk Oligosaccharide Lacto-N-Hexaose
title_full_unstemmed Chemoenzymatic Synthesis of Asymmetrically Branched Human Milk Oligosaccharide Lacto-N-Hexaose
title_short Chemoenzymatic Synthesis of Asymmetrically Branched Human Milk Oligosaccharide Lacto-N-Hexaose
title_sort chemoenzymatic synthesis of asymmetrically branched human milk oligosaccharide lacto-n-hexaose
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9194828/
https://www.ncbi.nlm.nih.gov/pubmed/35711960
http://dx.doi.org/10.3389/fchem.2022.905105
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