Directed evolution of enzymatic silicon-carbon bond cleavage in siloxanes
Volatile methylsiloxanes (VMS) are man-made, nonbiodegradable chemicals produced at a megaton-per-year scale, which leads to concern over their potential for environmental persistence, long-range transport, and bioaccumulation. We used directed evolution to engineer a variant of bacterial cytochrome...
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| Published in | Science (American Association for the Advancement of Science) Vol. 383; no. 6681; pp. 438 - 443 |
|---|---|
| Main Authors | , , , , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
Amer Assoc Advancement Science
26.01.2024
The American Association for the Advancement of Science |
| Subjects | |
| Online Access | Get full text |
| ISSN | 0036-8075 1095-9203 1095-9203 |
| DOI | 10.1126/science.adi5554 |
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| Abstract | Volatile methylsiloxanes (VMS) are man-made, nonbiodegradable chemicals produced at a megaton-per-year scale, which leads to concern over their potential for environmental persistence, long-range transport, and bioaccumulation. We used directed evolution to engineer a variant of bacterial cytochrome P450
BM3
to break silicon-carbon bonds in linear and cyclic VMS. To accomplish silicon-carbon bond cleavage, the enzyme catalyzes two tandem oxidations of a siloxane methyl group, which is followed by putative [1,2]-Brook rearrangement and hydrolysis. Discovery of this so-called siloxane oxidase opens possibilities for the eventual biodegradation of VMS.
Methylsiloxanes are organosilicon compounds produced by humans for use in a wide range of consumer products. Because they are not naturally found in nature, they are not readily degraded by organisms and some also have the potential to bioaccumulate. Sarai
et al
. identified a cytochrome P450 enzyme that can perform a hydroxylation on the methyl groups of linear methylsiloxanes. They then expanded this activity using directed evolution, creating variants that were more efficient and also functioned on cyclic methylsiloxanes. Mechanistic experiments suggested that a second oxidation and an enzyme-facilitated rearrangement can lead to cleavage of the carbon–silicon bond and release of formaldehyde. —Michael A. Funk
An engineered enzyme catalyzes two sequential methyl group oxidations that lead to carbon–silicon bond cleavage in siloxanes. |
|---|---|
| AbstractList | Editor’s summaryMethylsiloxanes are organosilicon compounds produced by humans for use in a wide range of consumer products. Because they are not naturally found in nature, they are not readily degraded by organisms and some also have the potential to bioaccumulate. Sarai et al. identified a cytochrome P450 enzyme that can perform a hydroxylation on the methyl groups of linear methylsiloxanes. They then expanded this activity using directed evolution, creating variants that were more efficient and also functioned on cyclic methylsiloxanes. Mechanistic experiments suggested that a second oxidation and an enzyme-facilitated rearrangement can lead to cleavage of the carbon–silicon bond and release of formaldehyde. —Michael A. Funk Volatile methylsiloxanes (VMS) are man-made, nonbiodegradable chemicals produced at a megaton-per-year scale, which leads to concern over their potential for environmental persistence, long-range transport, and bioaccumulation. We used directed evolution to engineer a variant of bacterial cytochrome P450BM3 to break silicon-carbon bonds in linear and cyclic VMS. To accomplish silicon-carbon bond cleavage, the enzyme catalyzes two tandem oxidations of a siloxane methyl group, which is followed by putative [1,2]-Brook rearrangement and hydrolysis. Discovery of this so-called siloxane oxidase opens possibilities for the eventual biodegradation of VMS. Volatile methylsiloxanes (VMS) are man-made, nonbiodegradable chemicals produced at a megaton-per-year scale, which leads to concern over their potential for environmental persistence, long-range transport, and bioaccumulation. We used directed evolution to engineer a variant of bacterial cytochrome P450BM3 to break silicon-carbon bonds in linear and cyclic VMS. To accomplish silicon-carbon bond cleavage, the enzyme catalyzes two tandem oxidations of a siloxane methyl group, which is followed by putative [1,2]-Brook rearrangement and hydrolysis. Discovery of this so-called siloxane oxidase opens possibilities for the eventual biodegradation of VMS.Volatile methylsiloxanes (VMS) are man-made, nonbiodegradable chemicals produced at a megaton-per-year scale, which leads to concern over their potential for environmental persistence, long-range transport, and bioaccumulation. We used directed evolution to engineer a variant of bacterial cytochrome P450BM3 to break silicon-carbon bonds in linear and cyclic VMS. To accomplish silicon-carbon bond cleavage, the enzyme catalyzes two tandem oxidations of a siloxane methyl group, which is followed by putative [1,2]-Brook rearrangement and hydrolysis. Discovery of this so-called siloxane oxidase opens possibilities for the eventual biodegradation of VMS. Volatile methylsiloxanes (VMS) are man-made, nonbiodegradable chemicals produced at a megaton-per-year scale, which leads to concern over their potential for environmental persistence, long-range transport, and bioaccumulation. We used directed evolution to engineer a variant of bacterial cytochrome P450 to break silicon-carbon bonds in linear and cyclic VMS. To accomplish silicon-carbon bond cleavage, the enzyme catalyzes two tandem oxidations of a siloxane methyl group, which is followed by putative [1,2]-Brook rearrangement and hydrolysis. Discovery of this so-called siloxane oxidase opens possibilities for the eventual biodegradation of VMS. Volatile methylsiloxanes (VMS) are man-made, nonbiodegradable chemicals produced at a megaton-per-year scale, which leads to concern over their potential for environmental persistence, long-range transport, and bioaccumulation. We used directed evolution to engineer a variant of bacterial cytochrome P450 BM3 to break silicon-carbon bonds in linear and cyclic VMS. To accomplish silicon-carbon bond cleavage, the enzyme catalyzes two tandem oxidations of a siloxane methyl group, which is followed by putative [1,2]-Brook rearrangement and hydrolysis. Discovery of this so-called siloxane oxidase opens possibilities for the eventual biodegradation of VMS. Methylsiloxanes are organosilicon compounds produced by humans for use in a wide range of consumer products. Because they are not naturally found in nature, they are not readily degraded by organisms and some also have the potential to bioaccumulate. Sarai et al . identified a cytochrome P450 enzyme that can perform a hydroxylation on the methyl groups of linear methylsiloxanes. They then expanded this activity using directed evolution, creating variants that were more efficient and also functioned on cyclic methylsiloxanes. Mechanistic experiments suggested that a second oxidation and an enzyme-facilitated rearrangement can lead to cleavage of the carbon–silicon bond and release of formaldehyde. —Michael A. Funk An engineered enzyme catalyzes two sequential methyl group oxidations that lead to carbon–silicon bond cleavage in siloxanes. |
| Author | Sarai, Nicholas S. Arnold, Frances H. Brinkmann-Chen, Sabine Reddel, Jordan C. T. Tecklenburg, Ron E. Roberts, John M. Johnston, Kadina E. Fulton, Tyler J. O’Meara, Ryen L. Maar, Ryan R. Katsoulis, Dimitris E. |
| Author_xml | – sequence: 1 givenname: Nicholas S. orcidid: 0000-0002-4655-0038 surname: Sarai fullname: Sarai, Nicholas S. organization: Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA 91125, USA – sequence: 2 givenname: Tyler J. orcidid: 0000-0002-9343-2456 surname: Fulton fullname: Fulton, Tyler J. organization: Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA 91125, USA – sequence: 3 givenname: Ryen L. orcidid: 0000-0002-3868-0270 surname: O’Meara fullname: O’Meara, Ryen L. organization: Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA 91125, USA – sequence: 4 givenname: Kadina E. orcidid: 0000-0002-2214-3534 surname: Johnston fullname: Johnston, Kadina E. organization: Division of Biology and Biological Engineering, California Institute of Technology, Pasadena, CA 91125, USA – sequence: 5 givenname: Sabine orcidid: 0000-0002-5419-4192 surname: Brinkmann-Chen fullname: Brinkmann-Chen, Sabine organization: Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA 91125, USA – sequence: 6 givenname: Ryan R. orcidid: 0009-0002-3165-7489 surname: Maar fullname: Maar, Ryan R. organization: Core R&D, Dow Inc., Midland, MI 48674, USA – sequence: 7 givenname: Ron E. orcidid: 0009-0006-9948-9900 surname: Tecklenburg fullname: Tecklenburg, Ron E. organization: Core R&D, Dow Inc., Midland, MI 48674, USA – sequence: 8 givenname: John M. orcidid: 0000-0001-7733-6301 surname: Roberts fullname: Roberts, John M. organization: Core R&D, Dow Inc., Midland, MI 48674, USA – sequence: 9 givenname: Jordan C. T. orcidid: 0009-0008-6530-6488 surname: Reddel fullname: Reddel, Jordan C. T. organization: Core R&D, Dow Inc., Midland, MI 48674, USA – sequence: 10 givenname: Dimitris E. orcidid: 0000-0002-9855-038X surname: Katsoulis fullname: Katsoulis, Dimitris E. organization: Dow Silicones Corporation, Auburn, MI 48611, USA – sequence: 11 givenname: Frances H. orcidid: 0000-0002-4027-364X surname: Arnold fullname: Arnold, Frances H. organization: Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA 91125, USA |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/38271505$$D View this record in MEDLINE/PubMed |
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| Keywords | OCTAMETHYLCYCLOTETRASILOXANE CYTOCHROME-P450 METABOLITES KINETICS VOLATILE METHYL SILOXANES |
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| Snippet | Volatile methylsiloxanes (VMS) are man-made, nonbiodegradable chemicals produced at a megaton-per-year scale, which leads to concern over their potential for... Editor’s summaryMethylsiloxanes are organosilicon compounds produced by humans for use in a wide range of consumer products. Because they are not naturally... |
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| SubjectTerms | Bioaccumulation Carbon Cleavage Consumer products Cytochrome P450 Cytochromes P450 Directed evolution Evolution Hydroxylation Multidisciplinary Sciences Organosilicon compounds Oxidation Science & Technology Science & Technology - Other Topics Silicon Siloxanes |
| Title | Directed evolution of enzymatic silicon-carbon bond cleavage in siloxanes |
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