Exploiting the enantioselectivity of Baeyer-Villiger monooxygenases via boron oxidation

Patricia B. Brondani; Hanna Dudek; Joel S. Reis; Marco W. Fraaije; Leandro H. Andrade

doi:10.1016/j.tetasy.2012.05.004

Exploiting the enantioselectivity of Baeyer-Villiger monooxygenases via boron oxidation

Patricia B. Brondani
, Hanna Dudek
, Joel S. Reis
, Marco W. Fraaije
, Leandro H. Andrade^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › Academic › peer-review

19 Citations (Scopus)

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Abstract

The enantioselective carbon-boron bond oxidation of several chiral boron-containing compounds by Baeyer-Villiger monooxygenases was evaluated. PAMO and M446G PAMO conveniently oxidized 1-phenylethyl boronate into the corresponding 1-(phenyl)ethanol (ee = 82-91%). Cyclopropyl boronic esters were also oxidized but with no enantioselectivity. beta-Boryl carboxylic esters were not oxidized by any BVMOs. (C) 2012 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	703-708
Number of pages	6
Journal	Tetrahedron-Asymmetry
Volume	23
Issue number	9
DOIs	https://doi.org/10.1016/j.tetasy.2012.05.004
Publication status	Published - 15-May-2012

Keywords

CROSS-COUPLING REACTION
CYCLOHEXANONE OXYGENASE
PHENYLACETONE MONOOXYGENASE
1-ALKENYL HALIDES
VINYL PHOSPHATES
ESTERS
BIOCATALYSTS
BIS(PINACOLATO)DIBORON
IODIDES
ACID

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title = "Exploiting the enantioselectivity of Baeyer-Villiger monooxygenases via boron oxidation",

abstract = "The enantioselective carbon-boron bond oxidation of several chiral boron-containing compounds by Baeyer-Villiger monooxygenases was evaluated. PAMO and M446G PAMO conveniently oxidized 1-phenylethyl boronate into the corresponding 1-(phenyl)ethanol (ee = 82-91\%). Cyclopropyl boronic esters were also oxidized but with no enantioselectivity. beta-Boryl carboxylic esters were not oxidized by any BVMOs. (C) 2012 Elsevier Ltd. All rights reserved.",

keywords = "CROSS-COUPLING REACTION, CYCLOHEXANONE OXYGENASE, PHENYLACETONE MONOOXYGENASE, 1-ALKENYL HALIDES, VINYL PHOSPHATES, ESTERS, BIOCATALYSTS, BIS(PINACOLATO)DIBORON, IODIDES, ACID",

author = "Brondani, \{Patricia B.\} and Hanna Dudek and Reis, \{Joel S.\} and Fraaije, \{Marco W.\} and Andrade, \{Leandro H.\}",

year = "2012",

month = may,

day = "15",

doi = "10.1016/j.tetasy.2012.05.004",

language = "English",

volume = "23",

pages = "703--708",

journal = "Tetrahedron-Asymmetry",

issn = "0957-4166",

publisher = "PERGAMON-ELSEVIER SCIENCE LTD",

number = "9",

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TY - JOUR

T1 - Exploiting the enantioselectivity of Baeyer-Villiger monooxygenases via boron oxidation

AU - Brondani, Patricia B.

AU - Dudek, Hanna

AU - Reis, Joel S.

AU - Fraaije, Marco W.

AU - Andrade, Leandro H.

PY - 2012/5/15

Y1 - 2012/5/15

N2 - The enantioselective carbon-boron bond oxidation of several chiral boron-containing compounds by Baeyer-Villiger monooxygenases was evaluated. PAMO and M446G PAMO conveniently oxidized 1-phenylethyl boronate into the corresponding 1-(phenyl)ethanol (ee = 82-91%). Cyclopropyl boronic esters were also oxidized but with no enantioselectivity. beta-Boryl carboxylic esters were not oxidized by any BVMOs. (C) 2012 Elsevier Ltd. All rights reserved.

AB - The enantioselective carbon-boron bond oxidation of several chiral boron-containing compounds by Baeyer-Villiger monooxygenases was evaluated. PAMO and M446G PAMO conveniently oxidized 1-phenylethyl boronate into the corresponding 1-(phenyl)ethanol (ee = 82-91%). Cyclopropyl boronic esters were also oxidized but with no enantioselectivity. beta-Boryl carboxylic esters were not oxidized by any BVMOs. (C) 2012 Elsevier Ltd. All rights reserved.

KW - CROSS-COUPLING REACTION

KW - CYCLOHEXANONE OXYGENASE

KW - PHENYLACETONE MONOOXYGENASE

KW - 1-ALKENYL HALIDES

KW - VINYL PHOSPHATES

KW - ESTERS

KW - BIOCATALYSTS

KW - BIS(PINACOLATO)DIBORON

KW - IODIDES

KW - ACID

U2 - 10.1016/j.tetasy.2012.05.004

DO - 10.1016/j.tetasy.2012.05.004

M3 - Article

SN - 0957-4166

VL - 23

SP - 703

EP - 708

JO - Tetrahedron-Asymmetry

JF - Tetrahedron-Asymmetry

IS - 9

ER -

Exploiting the enantioselectivity of Baeyer-Villiger monooxygenases via boron oxidation

Abstract

Keywords

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