Biocatalytic stereoselective synthesis of methyl mandelates by engineering a cytochrome P450 hydroxylase

Xie, Ling-Zhi; Zhang, Yun; Zhang, Ruyue; Cui, Hao; Cui, Bao‐Dong; Han, Wen‐Yong; Wan, Nan‐Wei; Li, Zhi; Chen, Yong‐Zheng

doi:10.1016/j.gresc.2023.01.005

Cited by 5 publications

(3 citation statements)

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“…In our previous work, we have obtained several cytochrome P450 monooxygenases (P450DA, P450PL2-2) (Cui et al 2023 , 2019 ; Deng et al 2022 ; Wan et al 2022 ; Wang et al 2022 ; Xie et al 2020 , 2023 ) and also constructed five recombinant Escherichia coli strains (P450tol-1 to P450tol-5) harboring P450tol monooxygenase from Rhodococcus coprophilus TC-2 (Chen et al 2022 ; Li et al 2014 ) and five pairs of redox partner Fdx-FdR (ferredoxin-ferredoxin reductase) from P. lavamentivorans DS-1 (Wu et al 2018 ). With these P450s in hand, but-1-yn-1-ylbenzene ( 1a ) was used as a model substrate to explore the hydroxylation activity and stereoselectivity of these recombinant P450 strains.…”

Section: Resultsmentioning

confidence: 99%

“…However, P450s as an effective and versatile catalyst for the enantioselective hydroxylation of propargylic C-H bonds has not been available in literature. In light of our ongoing interests in P450s-catalyzed asymmetric hydroxylation reactions with a broad substrate range and widely applications (Cui et al 2023 , 2019 ; Deng et al 2022 ; Wan et al 2022 ; Wang et al 2022 ; Xie et al 2020 , 2023 ), we herein describe chiral propargylic alcohols were synthesized from the simple alkynes by P450tol catalyzed asymmetric propargylic C-H bonds hydroxylation with regio- and stereoselectivity (Fig. 1 b).…”

Section: Introductionmentioning

confidence: 99%

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Regioselective and enantioselective propargylic hydroxylations catalyzed by P450tol monooxygenases

Deng,

Song,

et al. 2024

Bioresour. Bioprocess.

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Regioselective and enantioselective hydroxylation of propargylic C-H bonds are useful reactions but often lack appropriate catalysts. Here a green and efficient asymmetric hydroxylation of primary and secondary C–H bonds at propargylic positions has been established. A series of optically active propargylic alcohols were prepared with high regio- and enantioselectivity (up to 99% ee) under mild reaction conditions by using P450tol, while the C≡C bonds in the molecule remained unreacted. This protocol provides a green and practical method for constructing enantiomerically chiral propargylic alcohols. In addition, we also demonstrated that the biohydroxylation strategy was able to scaled up to 2.25 mmol scale with the production of chiral propargyl alcohol 2a at a yield of 196 mg with 96% ee, which’s an important synthetic intermediate of antifungal drug Ravuconazole. Graphical Abstract

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Regioselective and enantioselective propargylic hydroxylations catalyzed by P450tol monooxygenases

Deng,

Song,

et al. 2024

Bioresour. Bioprocess.

Self Cite

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“…In light of our interest in discovering new P450s and solving the problems of chemo-, regio-, and stereoselectivity in asymmetric hydroxylation, we herein describe the development of P450DA mutants via structure-guided directed evolution for use as catalysts with enantioselective complementarity in the synthesis of chiral γ-halohydrins and β-haloallyl alcohols via C–H biohydroxylation of halohydrocarbons (Scheme c).…”

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confidence: 99%