Simultaneous cyclic deracemisation and stereoinversion of alcohols using orthogonal biocatalytic oxidation and reduction reactions
We developed a concurrent cyclic deracemisation approach for secondary alcohols that combines a non-stereospecific oxidation step and a stereoselective reduction step using two mutants of Thermoanaerobacter pseudoethanolicus secondary alcohol dehydrogenase ( Te SADH) that exhibit various extents of...
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Published in | Catalysis science & technology Vol. 1; no. 24; pp. 8213 - 8218 |
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Main Authors | , , , , |
Format | Journal Article |
Language | English |
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Royal Society of Chemistry
21.12.2020
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Abstract | We developed a concurrent cyclic deracemisation approach for secondary alcohols that combines a non-stereospecific oxidation step and a stereoselective reduction step using two mutants of
Thermoanaerobacter pseudoethanolicus
secondary alcohol dehydrogenase (
Te
SADH) that exhibit various extents of stereoselectivities. In this approach, W110G
Te
SADH, a sparingly stereoselective mutant, performs the non-stereospecific oxidation step and W110V/G198D
Te
SADH performs the stereoselective reduction step. The use of orthogonal cofactor regeneration systems allowed for the spontaneous operation of these mutants. (
S
)-Configured alcohols were obtained in moderate ee's from their racemates using this strategy. To our knowledge, this report provides the first example of a fully enzymatic cyclic deracemisation with a stereoselective reduction step (CD-RS) for alcohols. This approach was further improved into a deracemisation strategy
via
stereoinversion using concurrent (
R
)-selective I86A
Te
SADH-catalysed oxidation that leaves (
S
)-alcohols untouched and W110V/G198D
Te
SADH-catalysed stereoselective reduction of the resultant ketone intermediates into the corresponding (
S
)-configured alcohols. The latter strategy enabled quantitative production of (
S
)-1-phenylethanol in >99% ee from its racemate. Overall, we show the superiority of the stereoinversion deracemisation approach for alcohols when compared with cyclic deracemisation, which is mainly due to the elimination of futile cycles in the former.
We developed a concurrent cyclic deracemisation approach for secondary alcohols that combines a non-stereospecific oxidation step and a stereoselective reduction step using two mutants of
Te
SADH that exhibit various extents of stereoselectivities. |
---|---|
AbstractList | We developed a concurrent cyclic deracemisation approach for secondary alcohols that combines a non-stereospecific oxidation step and a stereoselective reduction step using two mutants of Thermoanaerobacter pseudoethanolicus secondary alcohol dehydrogenase (TeSADH) that exhibit various extents of stereoselectivities. In this approach, W110G TeSADH, a sparingly stereoselective mutant, performs the non-stereospecific oxidation step and W110V/G198D TeSADH performs the stereoselective reduction step. The use of orthogonal cofactor regeneration systems allowed for the spontaneous operation of these mutants. (S)-Configured alcohols were obtained in moderate ee's from their racemates using this strategy. To our knowledge, this report provides the first example of a fully enzymatic cyclic deracemisation with a stereoselective reduction step (CD-RS) for alcohols. This approach was further improved into a deracemisation strategy via stereoinversion using concurrent (R)-selective I86A TeSADH-catalysed oxidation that leaves (S)-alcohols untouched and W110V/G198D TeSADH-catalysed stereoselective reduction of the resultant ketone intermediates into the corresponding (S)-configured alcohols. The latter strategy enabled quantitative production of (S)-1-phenylethanol in >99% ee from its racemate. Overall, we show the superiority of the stereoinversion deracemisation approach for alcohols when compared with cyclic deracemisation, which is mainly due to the elimination of futile cycles in the former. We developed a concurrent cyclic deracemisation approach for secondary alcohols that combines a non-stereospecific oxidation step and a stereoselective reduction step using two mutants of Thermoanaerobacter pseudoethanolicus secondary alcohol dehydrogenase ( Te SADH) that exhibit various extents of stereoselectivities. In this approach, W110G Te SADH, a sparingly stereoselective mutant, performs the non-stereospecific oxidation step and W110V/G198D Te SADH performs the stereoselective reduction step. The use of orthogonal cofactor regeneration systems allowed for the spontaneous operation of these mutants. ( S )-Configured alcohols were obtained in moderate ee's from their racemates using this strategy. To our knowledge, this report provides the first example of a fully enzymatic cyclic deracemisation with a stereoselective reduction step (CD-RS) for alcohols. This approach was further improved into a deracemisation strategy via stereoinversion using concurrent ( R )-selective I86A Te SADH-catalysed oxidation that leaves ( S )-alcohols untouched and W110V/G198D Te SADH-catalysed stereoselective reduction of the resultant ketone intermediates into the corresponding ( S )-configured alcohols. The latter strategy enabled quantitative production of ( S )-1-phenylethanol in >99% ee from its racemate. Overall, we show the superiority of the stereoinversion deracemisation approach for alcohols when compared with cyclic deracemisation, which is mainly due to the elimination of futile cycles in the former. We developed a concurrent cyclic deracemisation approach for secondary alcohols that combines a non-stereospecific oxidation step and a stereoselective reduction step using two mutants of Thermoanaerobacter pseudoethanolicus secondary alcohol dehydrogenase ( Te SADH) that exhibit various extents of stereoselectivities. In this approach, W110G Te SADH, a sparingly stereoselective mutant, performs the non-stereospecific oxidation step and W110V/G198D Te SADH performs the stereoselective reduction step. The use of orthogonal cofactor regeneration systems allowed for the spontaneous operation of these mutants. ( S )-Configured alcohols were obtained in moderate ee's from their racemates using this strategy. To our knowledge, this report provides the first example of a fully enzymatic cyclic deracemisation with a stereoselective reduction step (CD-RS) for alcohols. This approach was further improved into a deracemisation strategy via stereoinversion using concurrent ( R )-selective I86A Te SADH-catalysed oxidation that leaves ( S )-alcohols untouched and W110V/G198D Te SADH-catalysed stereoselective reduction of the resultant ketone intermediates into the corresponding ( S )-configured alcohols. The latter strategy enabled quantitative production of ( S )-1-phenylethanol in >99% ee from its racemate. Overall, we show the superiority of the stereoinversion deracemisation approach for alcohols when compared with cyclic deracemisation, which is mainly due to the elimination of futile cycles in the former. We developed a concurrent cyclic deracemisation approach for secondary alcohols that combines a non-stereospecific oxidation step and a stereoselective reduction step using two mutants of Te SADH that exhibit various extents of stereoselectivities. |
Author | Takahashi, Etsuko Takahashi, Masateru Musa, Musa M Hamdan, Samir M Nafiu, Sodiq A |
AuthorAffiliation | Department of Chemistry Division of Biological and Environmental Sciences and Engineering King Fahd University of Petroleum and Minerals King Abdullah University of Science and Technology |
AuthorAffiliation_xml | – name: King Abdullah University of Science and Technology – name: Department of Chemistry – name: Division of Biological and Environmental Sciences and Engineering – name: King Fahd University of Petroleum and Minerals |
Author_xml | – sequence: 1 givenname: Sodiq A surname: Nafiu fullname: Nafiu, Sodiq A – sequence: 2 givenname: Masateru surname: Takahashi fullname: Takahashi, Masateru – sequence: 3 givenname: Etsuko surname: Takahashi fullname: Takahashi, Etsuko – sequence: 4 givenname: Samir M surname: Hamdan fullname: Hamdan, Samir M – sequence: 5 givenname: Musa M surname: Musa fullname: Musa, Musa M |
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CitedBy_id | crossref_primary_10_1002_cbic_202100043 crossref_primary_10_1016_j_ijbiomac_2024_132238 crossref_primary_10_1002_slct_202103178 crossref_primary_10_1016_j_cogsc_2021_100548 crossref_primary_10_1039_D2CY00145D crossref_primary_10_1002_anie_202107570 crossref_primary_10_1002_ange_202107570 |
Cites_doi | 10.1016/j.cbpa.2004.02.005 10.1016/j.tet.2011.11.014 10.1007/s10295-014-1558-5 10.1002/adsc.201500316 10.1039/C5RA18532G 10.1002/3527608184 10.1039/c3cs60175g 10.1002/ejoc.202000728 10.1016/j.molcatb.2008.07.011 10.1021/cs501457v 10.1039/C9CY01539F 10.1021/ja804816a 10.1039/C4OB00794H 10.1007/s00253-007-1002-0 10.1016/j.molcatb.2014.08.018 10.1016/j.molcatb.2014.09.016 10.1002/adsc.200606158 10.1039/c3cc46240d 10.1039/c0cc02813d 10.1002/chem.200701643 10.1016/j.jbiotec.2012.03.015 10.1002/cctc.200900033 10.1002/cctc.201600160 10.1021/jacs.5b01031 10.3109/10242422.2011.615925 10.1002/cctc.201300409 10.1128/AEM.54.2.460-465.1988 10.1002/ejoc.200900935 10.1016/j.tetasy.2012.09.014 10.1002/cctc.201701092 10.1002/cctc.201500816 10.1002/ejoc.201800569 10.1002/cctc.201601618 10.2174/2213346102666150120221227 10.1016/j.molcatb.2016.04.003 10.1039/c4gc00066h |
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Title | Simultaneous cyclic deracemisation and stereoinversion of alcohols using orthogonal biocatalytic oxidation and reduction reactions |
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