Enantioselective catalysts based on metal-organic framework-supported nucleotides

Danyu Wang; Zhe Li; Tian Yi Luo; Michael B. Schmithorst; Sunghwan Park; Wenqian Xu; Yurun Miao; Kaivalya Gawande; Chaoyun Tang; Brandon C. Bukowski; Bradley F. Chmelka; D. Howard Fairbrother; Efrosini Kokkoli; Michael Tsapatsis

doi:10.1016/j.micromeso.2023.112703

Enantioselective catalysts based on metal-organic framework-supported nucleotides

Danyu Wang, Zhe Li, Tian Yi Luo, Michael B. Schmithorst, Sunghwan Park, Wenqian Xu, Yurun Miao, Kaivalya Gawande, Chaoyun Tang, Brandon C. Bukowski, Bradley F. Chmelka, D. Howard Fairbrother, Efrosini Kokkoli, Michael Tsapatsis

Research output: Contribution to journal › Article › peer-review

Abstract

Adenosine triphosphate (ATP) and other nucleotides can be irreversibly bound to the metal-organic framework (MOF) MIL-101(Cr). Analysis of X-ray diffraction data suggests that the location of the adsorbed ATP molecule is in proximity of the Cr₃ clusters. Solid-state NMR and DFT calculations indicate that ATP is bound to MIL-101(Cr) through linkages of the terminal phosphate group with Cr(III) of the framework. In the presence of Cu(II) ions, the MOF-supported nucleotides can function as stable and reusable enantioselective heterogeneous catalysts for reactions like Diels-Alder and Michael addition. Compared to the corresponding homogeneous nucleotide-based artificial metalloenzymes (ArMs), the MOF-supported nucleotide-based ArMs exhibit significantly enhanced activity and selectivity in certain cases, demonstrating their potential as a new class of enantioselective heterogeneous catalysts.

Original language	English
Article number	112703
Journal	Microporous and Mesoporous Materials
Volume	360
DOIs	https://doi.org/10.1016/j.micromeso.2023.112703
State	Published - Oct 2023

Keywords

Artificial metalloenzyme
Asymmetric catalysis
Heterogenous catalysis
Metal-organic framework

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Wang, D., Li, Z., Luo, T. Y., Schmithorst, M. B., Park, S., Xu, W., Miao, Y., Gawande, K., Tang, C., Bukowski, B. C., Chmelka, B. F., Fairbrother, D. H., Kokkoli, E., & Tsapatsis, M. (2023). Enantioselective catalysts based on metal-organic framework-supported nucleotides. Microporous and Mesoporous Materials, 360, Article 112703. https://doi.org/10.1016/j.micromeso.2023.112703

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title = "Enantioselective catalysts based on metal-organic framework-supported nucleotides",

abstract = "Adenosine triphosphate (ATP) and other nucleotides can be irreversibly bound to the metal-organic framework (MOF) MIL-101(Cr). Analysis of X-ray diffraction data suggests that the location of the adsorbed ATP molecule is in proximity of the Cr3 clusters. Solid-state NMR and DFT calculations indicate that ATP is bound to MIL-101(Cr) through linkages of the terminal phosphate group with Cr(III) of the framework. In the presence of Cu(II) ions, the MOF-supported nucleotides can function as stable and reusable enantioselective heterogeneous catalysts for reactions like Diels-Alder and Michael addition. Compared to the corresponding homogeneous nucleotide-based artificial metalloenzymes (ArMs), the MOF-supported nucleotide-based ArMs exhibit significantly enhanced activity and selectivity in certain cases, demonstrating their potential as a new class of enantioselective heterogeneous catalysts.",

keywords = "Artificial metalloenzyme, Asymmetric catalysis, Heterogenous catalysis, Metal-organic framework",

author = "Danyu Wang and Zhe Li and Luo, {Tian Yi} and Schmithorst, {Michael B.} and Sunghwan Park and Wenqian Xu and Yurun Miao and Kaivalya Gawande and Chaoyun Tang and Bukowski, {Brandon C.} and Chmelka, {Bradley F.} and Fairbrother, {D. Howard} and Efrosini Kokkoli and Michael Tsapatsis",

note = "Publisher Copyright: {\textcopyright} 2023 Elsevier Inc.",

year = "2023",

month = oct,

doi = "10.1016/j.micromeso.2023.112703",

language = "English",

volume = "360",

journal = "Microporous and Mesoporous Materials",

issn = "1387-1811",

publisher = "Elsevier B.V.",

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T1 - Enantioselective catalysts based on metal-organic framework-supported nucleotides

AU - Wang, Danyu

AU - Li, Zhe

AU - Luo, Tian Yi

AU - Schmithorst, Michael B.

AU - Park, Sunghwan

AU - Xu, Wenqian

AU - Miao, Yurun

AU - Gawande, Kaivalya

AU - Tang, Chaoyun

AU - Bukowski, Brandon C.

AU - Chmelka, Bradley F.

AU - Fairbrother, D. Howard

AU - Kokkoli, Efrosini

AU - Tsapatsis, Michael

PY - 2023/10

Y1 - 2023/10

N2 - Adenosine triphosphate (ATP) and other nucleotides can be irreversibly bound to the metal-organic framework (MOF) MIL-101(Cr). Analysis of X-ray diffraction data suggests that the location of the adsorbed ATP molecule is in proximity of the Cr3 clusters. Solid-state NMR and DFT calculations indicate that ATP is bound to MIL-101(Cr) through linkages of the terminal phosphate group with Cr(III) of the framework. In the presence of Cu(II) ions, the MOF-supported nucleotides can function as stable and reusable enantioselective heterogeneous catalysts for reactions like Diels-Alder and Michael addition. Compared to the corresponding homogeneous nucleotide-based artificial metalloenzymes (ArMs), the MOF-supported nucleotide-based ArMs exhibit significantly enhanced activity and selectivity in certain cases, demonstrating their potential as a new class of enantioselective heterogeneous catalysts.

AB - Adenosine triphosphate (ATP) and other nucleotides can be irreversibly bound to the metal-organic framework (MOF) MIL-101(Cr). Analysis of X-ray diffraction data suggests that the location of the adsorbed ATP molecule is in proximity of the Cr3 clusters. Solid-state NMR and DFT calculations indicate that ATP is bound to MIL-101(Cr) through linkages of the terminal phosphate group with Cr(III) of the framework. In the presence of Cu(II) ions, the MOF-supported nucleotides can function as stable and reusable enantioselective heterogeneous catalysts for reactions like Diels-Alder and Michael addition. Compared to the corresponding homogeneous nucleotide-based artificial metalloenzymes (ArMs), the MOF-supported nucleotide-based ArMs exhibit significantly enhanced activity and selectivity in certain cases, demonstrating their potential as a new class of enantioselective heterogeneous catalysts.

KW - Artificial metalloenzyme

KW - Asymmetric catalysis

KW - Heterogenous catalysis

KW - Metal-organic framework

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U2 - 10.1016/j.micromeso.2023.112703

DO - 10.1016/j.micromeso.2023.112703

M3 - Article

AN - SCOPUS:85164227908

SN - 1387-1811

VL - 360

JO - Microporous and Mesoporous Materials

JF - Microporous and Mesoporous Materials

M1 - 112703

ER -

Enantioselective catalysts based on metal-organic framework-supported nucleotides

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