From Glucose to Polymers: A Continuous Chemoenzymatic Process.
chemoenzymatic processes
glucose
poly(orthoester)
polymer synthesis
sustainable chemistry
Journal
Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543
Informations de publication
Date de publication:
19 10 2020
19 10 2020
Historique:
received:
04
05
2020
revised:
29
06
2020
entrez:
15
1
2021
pubmed:
16
1
2021
medline:
16
1
2021
Statut:
ppublish
Résumé
Efforts to synthesize degradable polymers from renewable resources are deterred by technical and economic challenges; especially, the conversion of natural building blocks into polymerizable monomers is inefficient, requiring multistep synthesis and chromatographic purification. Herein we report a chemoenzymatic process to address these challenges. An enzymatic reaction system was designed that allows for regioselective functional group transformation, efficiently converting glucose into a polymerizable monomer in quantitative yield, thus removing the need for chromatographic purification. With this key success, we further designed a continuous, three-step process, which enabled the synthesis of a sugar polymer, sugar poly(orthoester), directly from glucose in high yield (73 % from glucose). This work may provide a proof-of-concept in developing technically and economically viable approaches to address the many issues associated with current petroleum-based polymers.
Identifiants
pubmed: 33448568
doi: 10.1002/anie.202006468
doi:
Types de publication
Journal Article
Research Support, U.S. Gov't, Non-P.H.S.
Langues
eng
Sous-ensembles de citation
IM
Pagination
18943-18947Informations de copyright
© 2020 Wiley‐VCH GmbH.
Références
Y. Zhu, C. Romain, C. K. Williams, Nature 2016, 540, 354–362.
R. Geyer, J. R. Jambeck, K. L. Law, Sci. Adv. 2017, 3, e1700782.
A. Celli, A. Gandini, C. Gioia, T. M. Lacerda, M. Vannini, M. Colonna in Chemicals and Fuels from Bio-Based Building Blocks, 1st ed., Wiley-VCH, Weinheim, 2016, pp. 275–314.
Ellen MacArthur Foundation Report—The New Plastics Economy, 2016, https://www.ellenmacarthurfoundation.org/assets/downloads/New-Plastics-Economy_Catalysing-Action_13-11-17.pdf.
S. L. Kristufek, K. T. Wacker, Y.-Y. T. Tsao, L. Su, K. L. Wooley, Nat. Prod. Rep. 2017, 34, 433–459.
A. L. Holmberg, K. H. Reno, R. P. Wool, I. I. I. T. H. Epps, Soft Matter 2014, 10, 7405–7424.
J. P. Jain, M. Sokolsky, N. Kumar, A. J. Domb, Polym. Rev. 2008, 48, 156–191.
L. Maisonneuve, T. Lebarbé, E. Grau, H. Cramail, Polym. Chem. 2013, 4, 5472–5517.
J. A. Galbis, M. de Garcua García-Martín, M. V. de Paz, E. Galbis, Chem. Rev. 2016, 116, 1600–1636.
R. Xiao, M. W. Grinstaff, Prog. Polym. Sci. 2017, 74, 78–116.
https://www.alibaba.com/showroom/glucose-price-per-ton.html.
G. Liu, J. Zhang, J. Bao, Bioprocess Biosyst. Eng. 2016, 39, 133–140.
B. Yang, Z. Dai, S.-Y. Ding, C. E. Wyman, Biofuels 2011, 2, 421–449.
A. S. Balijepalli, R. C. Sabatelle, M. Chen, B. Suki, M. W. Grinstaff, Angew. Chem. Int. Ed. 2020, 59, 704–710;
Angew. Chem. 2020, 132, 714–720.
E. L. Dane, M. W. Grinstaff, J. Am. Chem. Soc. 2012, 134, 16255–16264.
K. Mikami, A. T. Lonnecker, T. P. Gustafson, N. F. Zinnel, P.-J. Pai, D. H. Russell, K. L. Wooley, J. Am. Chem. Soc. 2013, 135, 6826–6829.
Y. Song, X. Ji, M. Dong, R. Li, Y.-N. Lin, H. Wang, K. L. Wooley, J. Am. Chem. Soc. 2018, 140, 16053–16057.
A. T. Lonnecker, Y. H. Lim, S. E. Felder, C. J. Besset, K. L. Wooley, Macromolecules 2016, 49, 7857–7867.
L. Li, Y. Xu, I. Milligan, L. Fu, E. A. Franckowiak, W. Du, Angew. Chem. Int. Ed. 2013, 52, 13699–13702;
Angew. Chem. 2013, 125, 13944–13947.
L. Li, E. A. Franckowiak, Y. Xu, E. McClain, W. Du, J. Polym. Sci. Part A 2013, 51, 3693–3699.
S. Maiti, S. Manna, J. Shen, A. P. Esser-Kahn, W. Du, J. Am. Chem. Soc. 2019, 141, 4510–4514.
L. Li, K. Knickelbein, L. Zhang, J. Wang, M. Obrinske, G. Z. Ma, L.-M. Zhang, L. Bitterman, W. Du, Chem. Commun. 2015, 51, 13078–13081.
L. Li, J. Wang, M. Obrinske, I. Milligan, K. O'Hara, L. Bitterman, W. Du, Chem. Commun. 2015, 51, 6972–6975.
C.-W. Chang, S.-S. Chang, C.-S. Chao, K.-K. T. Mong, Tetrahedron Lett. 2009, 50, 4536–4540.
J.-L. Montero, J.-Y. Winum, A. Leydet, M. Kamal, A. A. Pavia, J.-P. Roque, Carbohydr. Res. 1997, 297, 175–180.
H. M. Sweers, C. H. Wong, J. Am. Chem. Soc. 1986, 108, 6421–6422.
W. J. Hennen, H. M. Sweers, Y. F. Wang, C. H. Wong, J. Org. Chem. 1988, 53, 4939–4945.
M. Filice, J. M. Guisan, M. Terreni, J. M. Palomo, Nat. Protoc. 2012, 7, 1783–1796.
I. Bhushan, R. Parshad, G. N. Qazi, V. K. Gupta, J. Bioact. Compat. Polym. 2008, 23, 552–562.
S. K. Bajpai, S. Sharma, React. Funct. Polym. 2004, 59, 129–140.
P. Sikorski, F. Mo, G. Skjåk-Bræk, B. T. Stokke, Biomacromolecules 2007, 8, 2098–2103.
P. Gurikov, I. Smirnova, Gels 2018, 4, 14.
G. Fernandez-Lorente, J. M. Palomo, J. Cocca, C. Mateo, P. Moro, M. Terreni, R. Fernandez-Lafuente, J. M. Guisan, Tetrahedron 2003, 59, 5705–5711.
M. Terreni, R. Salvetti, L. Linati, R. Fernandez-Lafuente, G. Fernández-Lorente, A. Bastida, J. M. Guisan, Carbohydr. Res. 2002, 337, 1615–1621.
Note: A spinning airstream was introduced into the vessel, making a vortex of the solvent (to produce large surface area thereby facilitating the evaporation). Meanwhile, a house vacuum was connected to the reaction vessel and the solvent was collected in a cold trap.
Y. Yu, S. Gim, D. Kim, Z. A. Arnon, E. Gazit, P. H. Seeberger, M. Delbianco, J. Am. Chem. Soc. 2019, 141, 4833–4838.
G. Odian, Principles of Polymerization. Introduction, 4th ed., Wiley, Hoboken, 2004.