Biomimetic oxidative copolymerization of hydroxystilbenes and monolignols

Biomimetic oxidative copolymerization of hydroxystilbenes and monolignols

18 páginas.- 6 figuras.- 4 tablas.- 92 referencias.-Supplementary Materials

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Main Authors: Kim, Hoon, Rencoret, Jorge, Elder T., Río Andrade, José Carlos del, Ralph, John
Other Authors: Great Lakes Bioenergy Research Center (US)
Format: artículo biblioteca
Language:English
Published: American Association for the Advancement of Science 2023-03-08
Online Access:http://hdl.handle.net/10261/297257
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spelling dig-irnas-es-10261-2972572023-03-10T13:37:07Z Biomimetic oxidative copolymerization of hydroxystilbenes and monolignols Kim, Hoon Rencoret, Jorge Elder T. Río Andrade, José Carlos del Ralph, John Great Lakes Bioenergy Research Center (US) DOE BER Office of Science Ministerio de Ciencia e Innovación (España) Agencia Estatal de Investigación (España) European Commission Junta de Andalucía Extreme Science and Engineering Discovery Environment (US) National Science Foundation (US) US Forest Service Kim, Hoon [0000-0001-7425-7464] Rencoret, Jorge [0000-0003-2728-7331] Elder T. [0000-0003-3909-2152] Río Andrade, José Carlos del [0000-0002-3040-6787] Ralph, John [0000-0002-6093-4521] 18 páginas.- 6 figuras.- 4 tablas.- 92 referencias.-Supplementary Materials ydroxystilbenes are a class of polyphenolic compounds that behave as lignin monomers participating in radical coupling reactions during the lignification. Here, we report the synthesis and characterization of various artificial copolymers of monolignols and hydroxystilbenes, as well as low-molecular-mass compounds, to obtain the mechanistic insights into their incorporation into the lignin polymer. Integrating the hydroxystilbenes, resveratrol and piceatannol, into monolignol polymerization in vitro, using horseradish peroxidase to generate phenolic radicals, produced synthetic lignins [dehydrogenation polymers (DHPs)]. Copolymerization of hydroxystilbenes with monolignols, especially sinapyl alcohol, by in vitro peroxidases notably improved the reactivity of monolignols and resulted in substantial yields of synthetic lignin polymers. The resulting DHPs were analyzed using two-dimensional NMR and 19 synthesized model compounds to confirm the presence of hydroxystilbene structures in the lignin polymer. The cross-coupled DHPs confirmed both resveratrol and piceatannol as authentic monomers participating in the oxidative radical coupling reactions during polymerization. This work was supported by grants from the DOE Great Lakes Bioenergy Research Center, and H.K. and J.Ra. were funded by the DOE BER Office of Science (DE- SC0018409). J.Re. and J.C.d.R. were supported by the projects AGL2017-83036-R and PID2020-118968RB-I00 (funded by MCIN/AEI/10.13039/501100011033 and, as appropriate, by “ERDF A way of making Europe”) and by the Andalusian Regional Government (project P20-00017). T.J.E. was funded by the Extreme Science and Engineering Discovery Environment (XSEDE), supported by the National Science Foundation grant number ACI-1548562. This work was made possible in part by a grant for high-performance computing resources and technical support from the Alabama Supercomputer Authority. This research was supported in part by the U.S. Department of Agriculture, U.S. Forest Service. Peer reviewed 2023-03-10T13:37:07Z 2023-03-10T13:37:07Z 2023-03-08 artículo Science advances 9(10): (2023) https://doi.org/10.1126/sciadv.ade5519 http://hdl.handle.net/10261/297257 10.1126/sciadv.ade5519 2375-2548 en #PLACEHOLDER_PARENT_METADATA_VALUE# #PLACEHOLDER_PARENT_METADATA_VALUE# #PLACEHOLDER_PARENT_METADATA_VALUE# info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/AGL2017-83036-R/ES/LIGNINAS DE RESIDUOS LIGNOCELULOSICOS DE LA ACTIVIDAD AGRICOLA: ESTRUCTURA QUIMICA Y VALORIZACION/ info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/PID2020-118968RB-I00/ES/LIGNINAS Y LIPIDOS: FUENTES RENOVABLES DE NUEVOS BIOPRODUCTOS/ info:eu-repo/grantAgreement/Junta de Andalucía/Plan Andaluz de Investigación, Desarrollo e Innovación (PAIDI 2020)/P20-00017 Publisher's version http://dx.doi.org/10.1126/sciadv.ade5519 Sí open American Association for the Advancement of Science
institution IRNAS ES
collection DSpace
country España
countrycode ES
component Bibliográfico
access En linea
databasecode dig-irnas-es
tag biblioteca
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libraryname Biblioteca del IRNAS España
language English
description 18 páginas.- 6 figuras.- 4 tablas.- 92 referencias.-Supplementary Materials
author2 Great Lakes Bioenergy Research Center (US)
author_facet Great Lakes Bioenergy Research Center (US)
Kim, Hoon
Rencoret, Jorge
Elder T.
Río Andrade, José Carlos del
Ralph, John
format artículo
author Kim, Hoon
Rencoret, Jorge
Elder T.
Río Andrade, José Carlos del
Ralph, John
spellingShingle Kim, Hoon
Rencoret, Jorge
Elder T.
Río Andrade, José Carlos del
Ralph, John
Biomimetic oxidative copolymerization of hydroxystilbenes and monolignols
author_sort Kim, Hoon
title Biomimetic oxidative copolymerization of hydroxystilbenes and monolignols
title_short Biomimetic oxidative copolymerization of hydroxystilbenes and monolignols
title_full Biomimetic oxidative copolymerization of hydroxystilbenes and monolignols
title_fullStr Biomimetic oxidative copolymerization of hydroxystilbenes and monolignols
title_full_unstemmed Biomimetic oxidative copolymerization of hydroxystilbenes and monolignols
title_sort biomimetic oxidative copolymerization of hydroxystilbenes and monolignols
publisher American Association for the Advancement of Science
publishDate 2023-03-08
url http://hdl.handle.net/10261/297257
work_keys_str_mv AT kimhoon biomimeticoxidativecopolymerizationofhydroxystilbenesandmonolignols
AT rencoretjorge biomimeticoxidativecopolymerizationofhydroxystilbenesandmonolignols
AT eldert biomimeticoxidativecopolymerizationofhydroxystilbenesandmonolignols
AT rioandradejosecarlosdel biomimeticoxidativecopolymerizationofhydroxystilbenesandmonolignols
AT ralphjohn biomimeticoxidativecopolymerizationofhydroxystilbenesandmonolignols
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