One-pot deracemization of sec-alcohols: Enantioconvergent enzymatic hydrolysis of alkyl sulfates using stereocomplementary sulfatases

Markus Schober; Michael Toesch; Tanja Knaus; Gernot A. Strohmeier; Bert Van Loo; Michael Fuchs; Florian Hollfelder; Peter Macheroux; Kurt Faber

doi:10.1002/anie.201209946

One-pot deracemization of sec-alcohols: Enantioconvergent enzymatic hydrolysis of alkyl sulfates using stereocomplementary sulfatases

Markus Schober^*, Michael Toesch, Tanja Knaus, Gernot A. Strohmeier, Bert Van Loo, Michael Fuchs, Florian Hollfelder, Peter Macheroux, Kurt Faber

^*Corresponding author for this work

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

27 Citations (Scopus)

50 Downloads (Pure)

Abstract

Hand in hand: The title transformation was achieved using a pair of sulfatases acting through inversion and retention of configuration on opposite substrate enantiomers. Using Pseudomonas aeruginosa arylsulfatase PAS with alkylsulfatase PISA1 in one-pot leads to sec-alcohols (80 to >99 % conversion) with 91 to greater than 99 % ee.

Original language	English
Pages (from-to)	3277-3279
Number of pages	3
Journal	Angewandte Chemie - International Edition
Volume	52
Issue number	11
DOIs	https://doi.org/10.1002/anie.201209946
Publication status	Published - 11 Mar 2013
Externally published	Yes

Keywords

alcohols
biotransformations
enzyme catalysis
kinetic resolution
synthetic methods

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10.1002/anie.201209946Licence: CC BY

Schober_et_al-2013-Angewandte_Chemie_International_EditionFinal published version, 411 KBLicence: CC BY

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title = "One-pot deracemization of sec-alcohols: Enantioconvergent enzymatic hydrolysis of alkyl sulfates using stereocomplementary sulfatases",

abstract = "Hand in hand: The title transformation was achieved using a pair of sulfatases acting through inversion and retention of configuration on opposite substrate enantiomers. Using Pseudomonas aeruginosa arylsulfatase PAS with alkylsulfatase PISA1 in one-pot leads to sec-alcohols (80 to >99 \% conversion) with 91 to greater than 99 \% ee.",

keywords = "alcohols, biotransformations, enzyme catalysis, kinetic resolution, synthetic methods",

author = "Markus Schober and Michael Toesch and Tanja Knaus and Strohmeier, \{Gernot A.\} and \{Van Loo\}, Bert and Michael Fuchs and Florian Hollfelder and Peter Macheroux and Kurt Faber",

year = "2013",

month = mar,

day = "11",

doi = "10.1002/anie.201209946",

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T2 - Enantioconvergent enzymatic hydrolysis of alkyl sulfates using stereocomplementary sulfatases

AU - Schober, Markus

AU - Toesch, Michael

AU - Knaus, Tanja

AU - Strohmeier, Gernot A.

AU - Van Loo, Bert

AU - Fuchs, Michael

AU - Hollfelder, Florian

AU - Macheroux, Peter

AU - Faber, Kurt

PY - 2013/3/11

Y1 - 2013/3/11

N2 - Hand in hand: The title transformation was achieved using a pair of sulfatases acting through inversion and retention of configuration on opposite substrate enantiomers. Using Pseudomonas aeruginosa arylsulfatase PAS with alkylsulfatase PISA1 in one-pot leads to sec-alcohols (80 to >99 % conversion) with 91 to greater than 99 % ee.

AB - Hand in hand: The title transformation was achieved using a pair of sulfatases acting through inversion and retention of configuration on opposite substrate enantiomers. Using Pseudomonas aeruginosa arylsulfatase PAS with alkylsulfatase PISA1 in one-pot leads to sec-alcohols (80 to >99 % conversion) with 91 to greater than 99 % ee.

KW - alcohols

KW - biotransformations

KW - enzyme catalysis

KW - kinetic resolution

KW - synthetic methods

UR - https://www.scopus.com/pages/publications/84874834871

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DO - 10.1002/anie.201209946

M3 - Article

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AN - SCOPUS:84874834871

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 11

ER -

One-pot deracemization of sec-alcohols: Enantioconvergent enzymatic hydrolysis of alkyl sulfates using stereocomplementary sulfatases

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Keywords

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