Please use this identifier to cite or link to this item: https://doi.org/10.1021/cs400992z
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dc.titleEnantioselective trans-dihydroxylation of aryl olefins by cascade biocatalysis with recombinant escherichia coli coexpressing monooxygenase and epoxide hydrolase
dc.contributor.authorWu, S.
dc.contributor.authorChen, Y.
dc.contributor.authorXu, Y.
dc.contributor.authorLi, A.
dc.contributor.authorXu, Q.
dc.contributor.authorGlieder, A.
dc.contributor.authorLi, Z.
dc.date.accessioned2014-10-09T06:46:51Z
dc.date.available2014-10-09T06:46:51Z
dc.date.issued2014-02-07
dc.identifier.citationWu, S., Chen, Y., Xu, Y., Li, A., Xu, Q., Glieder, A., Li, Z. (2014-02-07). Enantioselective trans-dihydroxylation of aryl olefins by cascade biocatalysis with recombinant escherichia coli coexpressing monooxygenase and epoxide hydrolase. ACS Catalysis 4 (2) : 409-420. ScholarBank@NUS Repository. https://doi.org/10.1021/cs400992z
dc.identifier.issn21555435
dc.identifier.urihttp://scholarbank.nus.edu.sg/handle/10635/88835
dc.description.abstractCascade biocatalysis via intracellular epoxidation and hydrolysis was developed as a green and efficient method for enantioselective dihydroxylation of aryl olefins to prepare chiral vicinal diols in high ee and high yield. Escherichia coli (SSP1) coexpressing styrene monooxygenase (SMO) and epoxide hydrolase SpEH was developed as a simple and efficient biocatalyst for S-enantioselective dihydroxylation of terminal aryl olefins 1a-15a to give (S)-vicinal diols 1c-15c in high ee (97.5-98.6% for 10 diols; 92.2-93.9% for 3 diols) and high yield (91-99% for 6 diols; 86-88% for 2 diols; 67% for 3 diols). Combining SMO and epoxide hydrolase StEH showing complementary regioselectivity to SpEH as a biocatalyst for the cascade biocatalysis gave rise to R-enantioselective dihydroxylation of aryl olefins, being the first example of this kind of reversing the overall enantioselectivity of cascade biocatalysis. E. coli (SST1) coexpressing SMO and StEH was also engineered as a green and efficient biocatalyst for R-dihydroxylation of terminal aryl olefins 1a-15a to give (R)-vicinal diols 1c-15c in high ee (94.2-98.2% for 7 diols; 84.2-89.9% for 6 diols) and high yield (90-99% for 6 diols; 85-89% for 5 diols; 65% for 1 diol). E. coli (SSP1) and E. coli (SST1) catalyzed the trans-dihydroxylation of trans-aryl olefin 16a and cis-aryl olefin 17a with excellent and complementary stereoselectivity, giving each of the four stereoisomers of 1-phenyl-1,2- propanediol 16c in high ee and de, respectively. Both strains catalyzed the trans-dihydroxylation of aryl cyclic olefins 18a and 19a to afford the same trans-cyclic diols (1R,2R)-18c and (1R,2R)-19c, respectively, in excellent ee and de. This type of cascade biocatalysis provides a tool that is complementary to Sharpless dihydroxylation, accepting cis-alkene and offering enantioselective trans-dihydroxylation. © 2013 American Chemical Society.
dc.description.urihttp://libproxy1.nus.edu.sg/login?url=http://dx.doi.org/10.1021/cs400992z
dc.sourceScopus
dc.subjectbiocatalysis
dc.subjectbiotransformations
dc.subjectcascade catalysis
dc.subjectdihydroxylation
dc.subjectenantioselectivity
dc.subjectepoxide hydrolase
dc.subjectmonooxygenase
dc.subjectvicinal diol
dc.typeArticle
dc.contributor.departmentCHEMICAL & BIOMOLECULAR ENGINEERING
dc.description.doi10.1021/cs400992z
dc.description.sourcetitleACS Catalysis
dc.description.volume4
dc.description.issue2
dc.description.page409-420
dc.description.codenACCAC
dc.identifier.isiut000331164000006
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