Arylboronic acids catalyzed upgrade of glucosamines for deoxyfructosazine and insights on reaction mechanism

Chitin is the most abundant N-containing polysaccharide in nature and d-glucosamine is one of the most successful commercial monomer products in the current market. Here we reported an arylboronic acids catalyzed upgrade of glucosamines in aqueous solution for deoxyfructosazine which is an important...

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Main Authors: Meifeng Wang, Gan Zhu, Yiqun Li, Liuqun Gu
Format: Article
Language:English
Published: Elsevier 2022-01-01
Series:Current Research in Green and Sustainable Chemistry
Subjects:
Online Access:http://www.sciencedirect.com/science/article/pii/S2666086522000509
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author Meifeng Wang
Gan Zhu
Yiqun Li
Liuqun Gu
author_facet Meifeng Wang
Gan Zhu
Yiqun Li
Liuqun Gu
author_sort Meifeng Wang
collection DOAJ
description Chitin is the most abundant N-containing polysaccharide in nature and d-glucosamine is one of the most successful commercial monomer products in the current market. Here we reported an arylboronic acids catalyzed upgrade of glucosamines in aqueous solution for deoxyfructosazine which is an important high-value compound in pharmaceutical and food industries, as well as a promising bio-based platform molecule for speciality chemicals and sustainable functional materials. Such direct integration of deoxyfructosazine into development of renewable chemicals/functional materials might be a practical way for utilization of chitin as a renewable nitrogen source. A mechanism focusing on a catalytic cycle of arylboronic acid via a boron transfer was also proposed.
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spelling doaj.art-3031c8df12ed4f0f8f536564bdf527122022-12-22T02:59:58ZengElsevierCurrent Research in Green and Sustainable Chemistry2666-08652022-01-015100308Arylboronic acids catalyzed upgrade of glucosamines for deoxyfructosazine and insights on reaction mechanismMeifeng Wang0Gan Zhu1Yiqun Li2Liuqun Gu3Department of Biomedical Engineering, Jinan University, #601, Huangpu Avenue West, Guangzhou, China; Department of Chemistry, Jinan University, #601, Huangpu Avenue West, Guangzhou, ChinaDepartment of Biomedical Engineering, Jinan University, #601, Huangpu Avenue West, Guangzhou, China; Department of Chemistry, Jinan University, #601, Huangpu Avenue West, Guangzhou, ChinaDepartment of Chemistry, Jinan University, #601, Huangpu Avenue West, Guangzhou, China; Corresponding authors.Department of Biomedical Engineering, Jinan University, #601, Huangpu Avenue West, Guangzhou, China; Corresponding authors.Chitin is the most abundant N-containing polysaccharide in nature and d-glucosamine is one of the most successful commercial monomer products in the current market. Here we reported an arylboronic acids catalyzed upgrade of glucosamines in aqueous solution for deoxyfructosazine which is an important high-value compound in pharmaceutical and food industries, as well as a promising bio-based platform molecule for speciality chemicals and sustainable functional materials. Such direct integration of deoxyfructosazine into development of renewable chemicals/functional materials might be a practical way for utilization of chitin as a renewable nitrogen source. A mechanism focusing on a catalytic cycle of arylboronic acid via a boron transfer was also proposed.http://www.sciencedirect.com/science/article/pii/S2666086522000509ChitinGlucosamineArylboronic acid catalysisDeoxyfructosazineAqueous solution
spellingShingle Meifeng Wang
Gan Zhu
Yiqun Li
Liuqun Gu
Arylboronic acids catalyzed upgrade of glucosamines for deoxyfructosazine and insights on reaction mechanism
Current Research in Green and Sustainable Chemistry
Chitin
Glucosamine
Arylboronic acid catalysis
Deoxyfructosazine
Aqueous solution
title Arylboronic acids catalyzed upgrade of glucosamines for deoxyfructosazine and insights on reaction mechanism
title_full Arylboronic acids catalyzed upgrade of glucosamines for deoxyfructosazine and insights on reaction mechanism
title_fullStr Arylboronic acids catalyzed upgrade of glucosamines for deoxyfructosazine and insights on reaction mechanism
title_full_unstemmed Arylboronic acids catalyzed upgrade of glucosamines for deoxyfructosazine and insights on reaction mechanism
title_short Arylboronic acids catalyzed upgrade of glucosamines for deoxyfructosazine and insights on reaction mechanism
title_sort arylboronic acids catalyzed upgrade of glucosamines for deoxyfructosazine and insights on reaction mechanism
topic Chitin
Glucosamine
Arylboronic acid catalysis
Deoxyfructosazine
Aqueous solution
url http://www.sciencedirect.com/science/article/pii/S2666086522000509
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AT yiqunli arylboronicacidscatalyzedupgradeofglucosaminesfordeoxyfructosazineandinsightsonreactionmechanism
AT liuqungu arylboronicacidscatalyzedupgradeofglucosaminesfordeoxyfructosazineandinsightsonreactionmechanism