Alternate Heme Ligation Steers Activity and Selectivity in Engineered Cytochrome P450-Catalyzed Carbene-Transfer Reactions
We report a biocatalytic platform of engineered cytochrome P450 enzymes to carry out carbene-transfer reactions using a lactone-based carbene precursor. By simply altering the heme-ligating residue, we obtained two enzymes that catalyze olefin cyclopropanation (Ser) or S–H bond insertion (Cys). Both...
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| Published in | Journal of the American Chemical Society Vol. 140; no. 48; pp. 16402 - 16407 |
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| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
05.12.2018
Amer Chemical Soc |
| Subjects | |
| Online Access | Get full text |
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| Abstract | We report a biocatalytic platform of engineered cytochrome P450 enzymes to carry out carbene-transfer reactions using a lactone-based carbene precursor. By simply altering the heme-ligating residue, we obtained two enzymes that catalyze olefin cyclopropanation (Ser) or S–H bond insertion (Cys). Both enzymes exhibit high catalytic efficiency and stereoselectivity, thus enabling facile access to structurally diverse spiro[2.4]lactones and α-thio-γ-lactones. Computational studies revealed the mechanism of carbene S–H insertion and explain how the axial ligand controls reactivity and selectivity. This work expands the catalytic repertoire of hemeproteins and offers insights into how these enzymes can be tuned for new chemistry. |
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| AbstractList | We report a biocatalytic platform of engineered cytochrome P450 enzymes to carry out carbene-transfer reactions using a lactone-based carbene precursor. By simply altering the heme-ligating residue, we obtained two enzymes that catalyze olefin cyclopropanation (Ser) or S-H bond insertion (Cys). Both enzymes exhibit high catalytic efficiency and stereoselectivity, thus enabling facile access to structurally diverse spiro[2.4]lactones and α-thio-γ-lactones. Computational studies revealed the mechanism of carbene S-H insertion and explain how the axial ligand controls reactivity and selectivity. This work expands the catalytic repertoire of hemeproteins and offers insights into how these enzymes can be tuned for new chemistry. We report a biocatalytic platform of engineered cytochrome P450 enzymes to carry out carbene-transfer reactions using a lactone-based carbene precursor. By simply altering the heme-ligating residue, we obtained two enzymes that catalyze olefin cyclopropanation (Ser) or S-H bond insertion (Cys). Both enzymes exhibit high catalytic efficiency and stereoselectivity, thus enabling facile access to structurally diverse spiro[2.4]lactones and α-thio-γ-lactones. Computational studies revealed the mechanism of carbene S-H insertion and explain how the axial ligand controls reactivity and selectivity. This work expands the catalytic repertoire of hemeproteins and offers insights into how these enzymes can be tuned for new chemistry.We report a biocatalytic platform of engineered cytochrome P450 enzymes to carry out carbene-transfer reactions using a lactone-based carbene precursor. By simply altering the heme-ligating residue, we obtained two enzymes that catalyze olefin cyclopropanation (Ser) or S-H bond insertion (Cys). Both enzymes exhibit high catalytic efficiency and stereoselectivity, thus enabling facile access to structurally diverse spiro[2.4]lactones and α-thio-γ-lactones. Computational studies revealed the mechanism of carbene S-H insertion and explain how the axial ligand controls reactivity and selectivity. This work expands the catalytic repertoire of hemeproteins and offers insights into how these enzymes can be tuned for new chemistry. We report a biocatalytic platform of engineered cytochrome P450 enzymes to carry out carbene-transfer reactions using a lactone-based carbene precursor. By simply altering the heme-ligating residue, we obtained two enzymes that catalyze olefin cyclopropanation (Ser) or S-H bond insertion (Cys). Both enzymes exhibit high catalytic efficiency and stereoselectivity, thus enabling facile access to structurally diverse spiro[2.4]-lactones and alpha-thio-gamma-lactones. Computational studies revealed the mechanism of carbene S-H insertion and explain how the axial ligand controls reactivity and selectivity. This work expands the catalytic repertoire of hemeproteins and offers insights into how these enzymes can be tuned for new chemistry. We report a biocatalytic platform of engineered cytochrome P450 enzymes to carry out carbene-transfer reactions using a lactone-based carbene precursor. By simply altering the heme-ligating residue, we obtained two enzymes that catalyze olefin cyclopropanation (Ser) or S–H bond insertion (Cys). Both enzymes exhibit high catalytic efficiency and stereoselectivity, thus enabling facile access to structurally diverse spiro[2.4]lactones and α-thio-γ-lactones. Computational studies revealed the mechanism of carbene S–H insertion and explain how the axial ligand controls reactivity and selectivity. This work expands the catalytic repertoire of hemeproteins and offers insights into how these enzymes can be tuned for new chemistry. |
| Author | Chen, Kai Zhang, Shuo-Qing Arnold, Frances H Brandenberg, Oliver F Hong, Xin |
| AuthorAffiliation | Department of Chemistry Division of Chemistry and Chemical Engineering 210-41 |
| AuthorAffiliation_xml | – name: Division of Chemistry and Chemical Engineering 210-41 – name: Department of Chemistry |
| Author_xml | – sequence: 1 givenname: Kai orcidid: 0000-0002-3325-3536 surname: Chen fullname: Chen, Kai organization: Division of Chemistry and Chemical Engineering 210-41 – sequence: 2 givenname: Shuo-Qing orcidid: 0000-0002-7617-3042 surname: Zhang fullname: Zhang, Shuo-Qing organization: Department of Chemistry – sequence: 3 givenname: Oliver F orcidid: 0000-0001-5662-1234 surname: Brandenberg fullname: Brandenberg, Oliver F organization: Division of Chemistry and Chemical Engineering 210-41 – sequence: 4 givenname: Xin orcidid: 0000-0003-4717-2814 surname: Hong fullname: Hong, Xin email: hxchem@zju.edu.cn organization: Department of Chemistry – sequence: 5 givenname: Frances H orcidid: 0000-0002-4027-364X surname: Arnold fullname: Arnold, Frances H email: frances@cheme.caltech.edu organization: Division of Chemistry and Chemical Engineering 210-41 |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/30372623$$D View this record in MEDLINE/PubMed |
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| Keywords | IRON PORPHYRIN CARBENES SUBSTITUENT INSERTION ENANTIOSELECTIVE S-H CONSTRUCTION CYCLOPROPANATION CATALYZED INTERMOLECULAR REACTIONS LACTONE BUILDING-BLOCKS BIOCATALYTIC PREPARATION |
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| Snippet | We report a biocatalytic platform of engineered cytochrome P450 enzymes to carry out carbene-transfer reactions using a lactone-based carbene precursor. By... |
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| SubjectTerms | carbenes catalytic activity chemical bonding Chemistry Chemistry, Multidisciplinary cytochrome P-450 enzymes heme lactones ligands olefin Physical Sciences Science & Technology steers stereoselectivity |
| Title | Alternate Heme Ligation Steers Activity and Selectivity in Engineered Cytochrome P450-Catalyzed Carbene-Transfer Reactions |
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