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Enzymatic synthesis of biobased aliphatic–aromatic oligoesters using 5,5′-bis(hydroxymethyl)furoin as a building block

5,5′-Dihydroxymethyl furoin (DHMF) is a novel biobased difuranic polyol scaffold, achievable from the benzoin condensation of 5-hydroxymethylfurfural (HMF), which has recently been employed as a monomer for the preparation of cross-linked polyesters and polyurethane. Its upgrading by means of enzyma...

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Autores principales: Baraldi, Serena, Fantin, Giancarlo, Di Carmine, Graziano, Ragno, Daniele, Brandolese, Arianna, Massi, Alessandro, Bortolini, Olga, Marchetti, Nicola, Giovannini, Pier Paolo
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9071804/
https://www.ncbi.nlm.nih.gov/pubmed/35528403
http://dx.doi.org/10.1039/c9ra06621g
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author Baraldi, Serena
Fantin, Giancarlo
Di Carmine, Graziano
Ragno, Daniele
Brandolese, Arianna
Massi, Alessandro
Bortolini, Olga
Marchetti, Nicola
Giovannini, Pier Paolo
author_facet Baraldi, Serena
Fantin, Giancarlo
Di Carmine, Graziano
Ragno, Daniele
Brandolese, Arianna
Massi, Alessandro
Bortolini, Olga
Marchetti, Nicola
Giovannini, Pier Paolo
author_sort Baraldi, Serena
collection PubMed
description 5,5′-Dihydroxymethyl furoin (DHMF) is a novel biobased difuranic polyol scaffold, achievable from the benzoin condensation of 5-hydroxymethylfurfural (HMF), which has recently been employed as a monomer for the preparation of cross-linked polyesters and polyurethane. Its upgrading by means of enzymatic reactions has not yet been reported. Here we demonstrated that Candida antarctica lipase B (CALB) is a suitable biocatalyst for the selective esterification of the primary hydroxyl groups of DHMF. Exploiting this enzymatic activity, DHMF has been reacted with the diethyl esters of succinic and sebacic acids obtaining fully biobased linear oligoesters with number-average molecular weight around 1000 g mol(−1) and free hydroxyl groups on the polymer backbone. The structures of the DHMF-diacid ethyl ester dimers and of the oligomers were elucidated by NMR and MS analyses.
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spelling pubmed-90718042022-05-06 Enzymatic synthesis of biobased aliphatic–aromatic oligoesters using 5,5′-bis(hydroxymethyl)furoin as a building block Baraldi, Serena Fantin, Giancarlo Di Carmine, Graziano Ragno, Daniele Brandolese, Arianna Massi, Alessandro Bortolini, Olga Marchetti, Nicola Giovannini, Pier Paolo RSC Adv Chemistry 5,5′-Dihydroxymethyl furoin (DHMF) is a novel biobased difuranic polyol scaffold, achievable from the benzoin condensation of 5-hydroxymethylfurfural (HMF), which has recently been employed as a monomer for the preparation of cross-linked polyesters and polyurethane. Its upgrading by means of enzymatic reactions has not yet been reported. Here we demonstrated that Candida antarctica lipase B (CALB) is a suitable biocatalyst for the selective esterification of the primary hydroxyl groups of DHMF. Exploiting this enzymatic activity, DHMF has been reacted with the diethyl esters of succinic and sebacic acids obtaining fully biobased linear oligoesters with number-average molecular weight around 1000 g mol(−1) and free hydroxyl groups on the polymer backbone. The structures of the DHMF-diacid ethyl ester dimers and of the oligomers were elucidated by NMR and MS analyses. The Royal Society of Chemistry 2019-09-16 /pmc/articles/PMC9071804/ /pubmed/35528403 http://dx.doi.org/10.1039/c9ra06621g Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Baraldi, Serena
Fantin, Giancarlo
Di Carmine, Graziano
Ragno, Daniele
Brandolese, Arianna
Massi, Alessandro
Bortolini, Olga
Marchetti, Nicola
Giovannini, Pier Paolo
Enzymatic synthesis of biobased aliphatic–aromatic oligoesters using 5,5′-bis(hydroxymethyl)furoin as a building block
title Enzymatic synthesis of biobased aliphatic–aromatic oligoesters using 5,5′-bis(hydroxymethyl)furoin as a building block
title_full Enzymatic synthesis of biobased aliphatic–aromatic oligoesters using 5,5′-bis(hydroxymethyl)furoin as a building block
title_fullStr Enzymatic synthesis of biobased aliphatic–aromatic oligoesters using 5,5′-bis(hydroxymethyl)furoin as a building block
title_full_unstemmed Enzymatic synthesis of biobased aliphatic–aromatic oligoesters using 5,5′-bis(hydroxymethyl)furoin as a building block
title_short Enzymatic synthesis of biobased aliphatic–aromatic oligoesters using 5,5′-bis(hydroxymethyl)furoin as a building block
title_sort enzymatic synthesis of biobased aliphatic–aromatic oligoesters using 5,5′-bis(hydroxymethyl)furoin as a building block
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9071804/
https://www.ncbi.nlm.nih.gov/pubmed/35528403
http://dx.doi.org/10.1039/c9ra06621g
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