Enzymatic Synthesis of 1,5-Anhydro-4-O-β-D-glucopyranosyl-D-fructose Using Cellobiose Phosphorylase and Its Spontaneous Decomposition via β-Elimination

Cellobiose phosphorylase from Cellvibrio gilvus was used to prepare 1,5-anhydro-4-O-β-D-glucopyranosyl-D-fructose [βGlc(1→4)AF] from 1,5-anhydro-D-fructose and α-D-glucose 1-phosphate. βGlc(1→4)AF decomposed into D-glucose and ascopyrone T via β-elimination. Higher pH and temperature caused faster d...

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Autores principales: Kajiki, Takahito, Yoshinaga, Kazuhiro, Komba, Shiro, Kitaoka, Motomitsu
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Japanese Society of Applied Glycoscience 2017
Materias:
Regular Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8056936/
https://www.ncbi.nlm.nih.gov/pubmed/34354501
http://dx.doi.org/10.5458/jag.jag.JAG-2017_010
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author Kajiki, Takahito
Yoshinaga, Kazuhiro
Komba, Shiro
Kitaoka, Motomitsu
author_facet Kajiki, Takahito
Yoshinaga, Kazuhiro
Komba, Shiro
Kitaoka, Motomitsu
author_sort Kajiki, Takahito
collection PubMed
description Cellobiose phosphorylase from Cellvibrio gilvus was used to prepare 1,5-anhydro-4-O-β-D-glucopyranosyl-D-fructose [βGlc(1→4)AF] from 1,5-anhydro-D-fructose and α-D-glucose 1-phosphate. βGlc(1→4)AF decomposed into D-glucose and ascopyrone T via β-elimination. Higher pH and temperature caused faster decomposition. However, decomposition proceeded significantly even under mild conditions. For instance, the half-life of βGlc(1→4)AF was 17 h at 30 °C and pH 7.0. Because βGlc(1→4)AF is a mimic of cellulose, in which the C2 hydroxyl group is oxidized, such decomposition may occur in oxidized cellulose in nature. Here we propose a possible oxidizing pathway by which this occurs.
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spelling pubmed-80569362021-08-04 Enzymatic Synthesis of 1,5-Anhydro-4-O-β-D-glucopyranosyl-D-fructose Using Cellobiose Phosphorylase and Its Spontaneous Decomposition via β-Elimination Kajiki, Takahito Yoshinaga, Kazuhiro Komba, Shiro Kitaoka, Motomitsu J Appl Glycosci (1999) Regular Paper Cellobiose phosphorylase from Cellvibrio gilvus was used to prepare 1,5-anhydro-4-O-β-D-glucopyranosyl-D-fructose [βGlc(1→4)AF] from 1,5-anhydro-D-fructose and α-D-glucose 1-phosphate. βGlc(1→4)AF decomposed into D-glucose and ascopyrone T via β-elimination. Higher pH and temperature caused faster decomposition. However, decomposition proceeded significantly even under mild conditions. For instance, the half-life of βGlc(1→4)AF was 17 h at 30 °C and pH 7.0. Because βGlc(1→4)AF is a mimic of cellulose, in which the C2 hydroxyl group is oxidized, such decomposition may occur in oxidized cellulose in nature. Here we propose a possible oxidizing pathway by which this occurs. The Japanese Society of Applied Glycoscience 2017-11-20 /pmc/articles/PMC8056936/ /pubmed/34354501 http://dx.doi.org/10.5458/jag.jag.JAG-2017_010 Text en 2017 by The Japanese Society of Applied Glycoscience https://creativecommons.org/licenses/by-nc/4.0/This is an open-access paper distributed under the terms of the Creative Commons Attribution Non-Commercial (by-nc) License (CC-BY-NC4.0: https://creativecommons.org/licenses/by-nc/4.0/).
spellingShingle Regular Paper
Kajiki, Takahito
Yoshinaga, Kazuhiro
Komba, Shiro
Kitaoka, Motomitsu
Enzymatic Synthesis of 1,5-Anhydro-4-O-β-D-glucopyranosyl-D-fructose Using Cellobiose Phosphorylase and Its Spontaneous Decomposition via β-Elimination
title Enzymatic Synthesis of 1,5-Anhydro-4-O-β-D-glucopyranosyl-D-fructose Using Cellobiose Phosphorylase and Its Spontaneous Decomposition via β-Elimination
title_full Enzymatic Synthesis of 1,5-Anhydro-4-O-β-D-glucopyranosyl-D-fructose Using Cellobiose Phosphorylase and Its Spontaneous Decomposition via β-Elimination
title_fullStr Enzymatic Synthesis of 1,5-Anhydro-4-O-β-D-glucopyranosyl-D-fructose Using Cellobiose Phosphorylase and Its Spontaneous Decomposition via β-Elimination
title_full_unstemmed Enzymatic Synthesis of 1,5-Anhydro-4-O-β-D-glucopyranosyl-D-fructose Using Cellobiose Phosphorylase and Its Spontaneous Decomposition via β-Elimination
title_short Enzymatic Synthesis of 1,5-Anhydro-4-O-β-D-glucopyranosyl-D-fructose Using Cellobiose Phosphorylase and Its Spontaneous Decomposition via β-Elimination
title_sort enzymatic synthesis of 1,5-anhydro-4-o-β-d-glucopyranosyl-d-fructose using cellobiose phosphorylase and its spontaneous decomposition via β-elimination
topic Regular Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8056936/
https://www.ncbi.nlm.nih.gov/pubmed/34354501
http://dx.doi.org/10.5458/jag.jag.JAG-2017_010
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