Biocatalytic Cascade Synthesis of Enantioenriched Epoxides and Triols from Biomass-Derived Synthons Driven by Specifically Designed Enzymes.
aldol reaction
asymmetric synthesis
cascade synthesis
enzyme catalysis
epoxidation
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
02 Jun 2023
02 Jun 2023
Historique:
received:
03
03
2023
medline:
5
6
2023
pubmed:
10
3
2023
entrez:
9
3
2023
Statut:
ppublish
Résumé
Multi-enzymatic cascades exploiting engineered enzymes are a powerful tool for the tailor-made synthesis of complex molecules from simple inexpensive building blocks. In this work, we engineered the promiscuous enzyme 4-oxalocrotonate tautomerase (4-OT) into an effective aldolase with 160-fold increased activity compared to 4-OT wild type. Subsequently, we applied the evolved 4-OT variant to perform an aldol condensation, followed by an epoxidation reaction catalyzed by a previously engineered 4-OT mutant, in a one-pot two-step cascade for the synthesis of enantioenriched epoxides (up to 98 % ee) from biomass-derived starting materials. For three chosen substrates, the reaction was performed at milligram scale with product yields up to 68 % and remarkably high enantioselectivity. Furthermore, we developed a three-step enzymatic cascade involving an epoxide hydrolase for the production of chiral aromatic 1,2,3-prim,sec,sec-triols with high enantiopurity and good isolated yields. The reported one-pot, three-step cascade, with no intermediate isolation and being completely cofactor-less, provides an attractive route for the synthesis of chiral aromatic triols from biomass-based synthons.
Identifiants
pubmed: 36893219
doi: 10.1002/chem.202300697
doi:
Substances chimiques
Epoxy Compounds
0
Aldehyde-Lyases
EC 4.1.2.-
Fructose-Bisphosphate Aldolase
EC 4.1.2.13
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202300697Subventions
Organisme : H2020 Marie Skłodowska-Curie Actions
ID : 723390
Organisme : Nederlandse Organisatie voor Wetenschappelijk Onderzoek
ID : 724.016.002
Informations de copyright
© 2023 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.
Références
F. Subrizi, Y. Wang, B. Thair, D. Méndez-Sánchez, R. Roddan, M. Cárdenas-Fernández, J. Siegrist, M. Richter, J. N. Andexer, J. M. Ward, et al., Angew. Chem. Int. Ed. 2021, 60, 18673-18679;
Angew. Chem. 2021, 133, 18821-18827.
V. Erdmann, T. Sehl, I. Frindi-Wosch, R. C. Simon, W. Kroutil, D. Rother, ACS Catal. 2019, 9, 7380-7388.
S. Sarak, S. Sung, H. Jeon, M. D. Patil, T. P. Khobragade, A. D. Pagar, P. E. Dawson, H. Yun, Angew. Chem. Int. Ed. 2021, 60, 3481-3486;
Angew. Chem. 2021, 133, 3523-3528.
Y. Zhou, S. Wu, Z. Li, Angew. Chem. Int. Ed. 2016, 55, 11647-11650;
Angew. Chem. 2016, 128, 11819-11822.
A. Li, A. Ilie, Z. Sun, R. Lonsdale, J.-H. Xu, M. T. Reetz, Angew. Chem. Int. Ed. 2016, 128, 12205-12208.
L. Biewenga, T. Saravanan, A. Kunzendorf, J. Y. Van Der Meer, T. Pijning, P. G. Tepper, R. Van Merkerk, S. J. Charnock, A. M. W. H. Thunnissen, G. J. Poelarends, ACS Catal. 2019, 9, 1503-1513.
L. Biewenga, A. Kunzendorf, G. J. Poelarends, ChemBioChem 2020, 21, 1505-1509.
E. Brenna, M. Crotti, F. G. Gatti, D. Monti, F. Parmeggiani, A. Pugliese, Molecules 2017, 22, 1-9.
E. Brenna, M. Crotti, F. G. Gatti, L. Marinoni, D. Monti, S. Quaiato, J. Org. Chem. 2017, 82, 2114-2122.
E. Brenna, M. Crotti, F. G. Gatti, D. Monti, F. Parmeggiani, A. Pugliese, F. Tentori, Green Chem. 2017, 19, 5122-5130.
C. Guo, M. Saifuddin, T. Saravanan, M. Sharifi, G. J. Poelarends, ACS Catal. 2019, 9, 4369-4373.
A. Kunzendorf, G. Xu, M. Saifuddin, T. Saravanan, G. J. Poelarends, Angew. Chem. Int. Ed. 2021, 60, 24059-24063;
Angew. Chem. 2021, 133, 24261-24265.
Y. Miao, P. G. Tepper, E. M. Geertsema, G. J. Poelarends, Eur. J. Org. Chem. 2016, 5350-5354.
E. Zandvoort, E. M. Geertsema, B. J. Baas, W. J. Quax, G. J. Poelarends, Angew. Chem. Int. Ed. 2012, 51, 1240-1243;
Angew. Chem. 2012, 124, 1266-1269.
Y. Miao, E. M. Geertsema, P. G. Tepper, E. Zandvoort, G. J. Poelarends, ChemBioChem 2013, 14, 191-194.
M. Rahimi, J. Y. Van der Meer, E. M. Geertsema, G. J. Poelarends, ChemBioChem 2017, 18, 1435-1441.
E. Zandvoort, E. M. Geertsema, W. J. Quax, G. J. Poelarends, ChemBioChem 2012, 13, 1274-1277.
M. Rahimi, E. M. Geertsema, Y. Miao, J. Y. Van Der Meer, T. Van Den Bosch, P. De Haan, E. Zandvoort, G. J. Poelarends, Org. Biomol. Chem. 2017, 15, 2809-2816.
M. Saifuddin, C. Guo, L. Biewenga, T. Saravanan, S. J. Charnock, G. J. Poelarends, ACS Catal. 2020, 10, 2522-2527.
G. Xu, M. Crotti, T. Saravanan, K. M. Kataja, G. J. Poelarends, Angew. Chem. Int. Ed. 2020, 59, 10374-10378;
Angew. Chem. 2020, 132, 10460-10464.
G. Xu, A. Kunzendorf, M. Crotti, H. J. Rozeboom, A. W. H. Thunnissen, G. J. Poelarends, Angew. Chem. Int. Ed. 2022, 61, e202113970.
M. C. Sigmund, G. Xu, E. Grandi, G. J. Poelarends, Chem. Eur. J. 2022, 28, e202201651.
X. Zhang, K. Z. Lu, H. W. Yan, Z. M. Feng, Y. N. Yang, J. S. Jiang, P. C. Zhang, RSC Adv. 2021, 11, 8107-8116.
G. L. Zhao, P. Dziedzic, I. Ibrahem, A. Córdova, Synlett 2006, 3, 3521-3524.
Z. X. Gao, M. Wang, S. Wang, Z. J. Yao, Org. Lett. 2009, 11, 3678-3681.
M. Von Itzstein, W. Y. Wu, G. B. Kok, M. S. Pegg, J. C. Dyason, B. Jin, T. Van Phan, M. L. Smythe, H. F. White, S. W. Oliver, et al., Nature 1993, 363, 418-423.
S. Li, X. P. Hui, S. B. Yang, Z. J. Jia, P. F. Xu, T. J. Lu, Tetrahedron: Asymmetry 2005, 16, 1729-1731.
A. R. Patel, X. G. Hu, A. Lawer, M. I. Ahmed, C. Au, R. Jwad, J. Trinh, C. Gonzalez, E. Hannah, M. M. Bhadbhade, et al., Tetrahedron 2016, 72, 3305-3317.
G. Chen, Z. Jiang, Q. Zhang, G. Wang, Q. H. Chen, Molecules 2020, 25, 10.3390/molecules25020362.
D. O. Usino, Supriyanto, P. Ylitervo, A. Pettersson, T. Richards, J. Anal. Appl. Pyrolysis 2020, 147, 104782.
P. D. Sainsbury, E. M. Hardiman, M. Ahmad, H. Otani, N. Seghezzi, L. D. Eltis, T. D. H. Bugg, ACS Chem. Biol. 2013, 8, 2151-2156.
J.-Y. Van der Meer, H. Poddar, B.-J. Baas, Y. Miao, M. Rahimi, A. Kunzendorf, R. Van Merkerk, P. G. Tepper, E. M. Geertsema, A.-M. W. H. Thunnissen, et al., Nat. Commun. 2016, 7, 10911.
L. Biewenga, M. Crotti, M. Saifuddin, G. J. Poelarends, ACS Omega 2020, 5, 2397-2405.
E. E. Ferrandi, C. Sayer, S. A. De Rose, E. Guazzelli, C. Marchesi, V. Saneei, M. N. Isupov, J. A. Littlechild, D. Monti, Front. Bioeng. Biotechnol. 2018, 6, 1-16.
J. Zhao, Y. Y. Chu, A. T. Li, X. Ju, X. D. Kong, J. Pan, Y. Tang, J. H. Xu, Adv. Synth. Catal. 2011, 353, 1510-1518.
Y. Shichijo, A. Migita, H. Oguri, M. Watanabe, T. Tokiwano, K. Watanabe, H. Oikawa, J. Am. Chem. Soc. 2008, 130, 12230-12231.
D. Pistorius, Y. Li, A. Sandmann, R. Müller, Mol. BioSyst. 2011, 7, 3308-3315.
E. Zandvoort, B. J. Baas, W. J. Quax, G. J. Poelarends, ChemBioChem 2011, 12, 602-609.
W. J. Waddell, J. Lab. Clin. Med. 1956, 48, 311-314.