A chemoenzymatic route to chiral siloxanes
An approach employing two enzymes—toluene dioxygenase and immobilized lipase B from Candida antarctica (N435)—was explored as a potential biocatalytic method for the coupling of chiral diols with siloxane species. Analysis of reaction mixtures using1H NMR spectroscopy suggested that up to 66% consum...
| Published in: | Tetrahedron |
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| Main Authors: | , , , , , |
| Format: | Text |
| Language: | unknown |
| Published: |
Scholarship at UWindsor
2016
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| Subjects: | |
| Online Access: | https://scholar.uwindsor.ca/chemistrybiochemistrypub/211 https://doi.org/10.1016/j.tet.2016.05.032 https://scholar.uwindsor.ca/context/chemistrybiochemistrypub/article/1213/viewcontent/21_Toward_the_Chemoenzymatic_Synthesis_of_Chiral_Siloxane_Polymers___Accepted.pdf |
| _version_ | 1821739344912711680 |
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| author | Naoum, Ravi Séguin, Jacqueline P. Trant, John F. Frampton, Mark B. Hudlický, Tomáš Zelisko, Paul M. |
| author_facet | Naoum, Ravi Séguin, Jacqueline P. Trant, John F. Frampton, Mark B. Hudlický, Tomáš Zelisko, Paul M. |
| author_sort | Naoum, Ravi |
| collection | University of Windsor, Ontario: Scholarship at UWindsor |
| container_issue | 27-28 |
| container_start_page | 4027 |
| container_title | Tetrahedron |
| container_volume | 72 |
| description | An approach employing two enzymes—toluene dioxygenase and immobilized lipase B from Candida antarctica (N435)—was explored as a potential biocatalytic method for the coupling of chiral diols with siloxane species. Analysis of reaction mixtures using1H NMR spectroscopy suggested that up to 66% consumption of the siloxane starting materials had occurred. Oligomeric species were observed and chiral products from the coupling of a cyclic diol with a siloxane molecule were isolated and characterized by MALDI-ToF MS and GPC. Immobilized lipases from Rhizomucor miehei and Thermomyces lanuginosus were also explored as potential catalysts for the coupling reactions, however, their use only returned starting material. |
| format | Text |
| genre | Antarc* Antarctica |
| genre_facet | Antarc* Antarctica |
| id | ftunivwindsor:oai:scholar.uwindsor.ca:chemistrybiochemistrypub-1213 |
| institution | Open Polar |
| language | unknown |
| op_collection_id | ftunivwindsor |
| op_container_end_page | 4031 |
| op_doi | https://doi.org/10.1016/j.tet.2016.05.032 |
| op_relation | https://scholar.uwindsor.ca/chemistrybiochemistrypub/211 doi:10.1016/j.tet.2016.05.032 https://scholar.uwindsor.ca/context/chemistrybiochemistrypub/article/1213/viewcontent/21_Toward_the_Chemoenzymatic_Synthesis_of_Chiral_Siloxane_Polymers___Accepted.pdf |
| op_source | Chemistry and Biochemistry Publications |
| publishDate | 2016 |
| publisher | Scholarship at UWindsor |
| record_format | openpolar |
| spelling | ftunivwindsor:oai:scholar.uwindsor.ca:chemistrybiochemistrypub-1213 2025-01-16T19:18:45+00:00 A chemoenzymatic route to chiral siloxanes Naoum, Ravi Séguin, Jacqueline P. Trant, John F. Frampton, Mark B. Hudlický, Tomáš Zelisko, Paul M. 2016-01-01T08:00:00Z application/pdf https://scholar.uwindsor.ca/chemistrybiochemistrypub/211 https://doi.org/10.1016/j.tet.2016.05.032 https://scholar.uwindsor.ca/context/chemistrybiochemistrypub/article/1213/viewcontent/21_Toward_the_Chemoenzymatic_Synthesis_of_Chiral_Siloxane_Polymers___Accepted.pdf unknown Scholarship at UWindsor https://scholar.uwindsor.ca/chemistrybiochemistrypub/211 doi:10.1016/j.tet.2016.05.032 https://scholar.uwindsor.ca/context/chemistrybiochemistrypub/article/1213/viewcontent/21_Toward_the_Chemoenzymatic_Synthesis_of_Chiral_Siloxane_Polymers___Accepted.pdf Chemistry and Biochemistry Publications Biotransformations Chemoenzymatic Chirality Siloxane Transesterification Biochemistry Biophysics and Structural Biology Chemistry text 2016 ftunivwindsor https://doi.org/10.1016/j.tet.2016.05.032 2023-05-06T19:10:57Z An approach employing two enzymes—toluene dioxygenase and immobilized lipase B from Candida antarctica (N435)—was explored as a potential biocatalytic method for the coupling of chiral diols with siloxane species. Analysis of reaction mixtures using1H NMR spectroscopy suggested that up to 66% consumption of the siloxane starting materials had occurred. Oligomeric species were observed and chiral products from the coupling of a cyclic diol with a siloxane molecule were isolated and characterized by MALDI-ToF MS and GPC. Immobilized lipases from Rhizomucor miehei and Thermomyces lanuginosus were also explored as potential catalysts for the coupling reactions, however, their use only returned starting material. Text Antarc* Antarctica University of Windsor, Ontario: Scholarship at UWindsor Tetrahedron 72 27-28 4027 4031 |
| spellingShingle | Biotransformations Chemoenzymatic Chirality Siloxane Transesterification Biochemistry Biophysics and Structural Biology Chemistry Naoum, Ravi Séguin, Jacqueline P. Trant, John F. Frampton, Mark B. Hudlický, Tomáš Zelisko, Paul M. A chemoenzymatic route to chiral siloxanes |
| title | A chemoenzymatic route to chiral siloxanes |
| title_full | A chemoenzymatic route to chiral siloxanes |
| title_fullStr | A chemoenzymatic route to chiral siloxanes |
| title_full_unstemmed | A chemoenzymatic route to chiral siloxanes |
| title_short | A chemoenzymatic route to chiral siloxanes |
| title_sort | chemoenzymatic route to chiral siloxanes |
| topic | Biotransformations Chemoenzymatic Chirality Siloxane Transesterification Biochemistry Biophysics and Structural Biology Chemistry |
| topic_facet | Biotransformations Chemoenzymatic Chirality Siloxane Transesterification Biochemistry Biophysics and Structural Biology Chemistry |
| url | https://scholar.uwindsor.ca/chemistrybiochemistrypub/211 https://doi.org/10.1016/j.tet.2016.05.032 https://scholar.uwindsor.ca/context/chemistrybiochemistrypub/article/1213/viewcontent/21_Toward_the_Chemoenzymatic_Synthesis_of_Chiral_Siloxane_Polymers___Accepted.pdf |