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Enantioselective Synthesis of α-Thiocarboxylic Acids by Nitrilase Biocatalysed Dynamic Kinetic Resolution of α-Thionitriles

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Enantioselective Synthesis of α-Thiocarboxylic Acids by Nitrilase Biocatalysed Dynamic Kinetic Resolution of α-Thionitriles. / Lauder, Kate; Anselmi, Silvia; Finnigan, James D.; Qi, Yuyin; Charnock, Simon J.; Castagnolo, Daniele.

In: Chemistry - A European Journal, Vol. 26, No. 46, 17.08.2020, p. 10422-10426.

Research output: Contribution to journalArticle

Harvard

Lauder, K, Anselmi, S, Finnigan, JD, Qi, Y, Charnock, SJ & Castagnolo, D 2020, 'Enantioselective Synthesis of α-Thiocarboxylic Acids by Nitrilase Biocatalysed Dynamic Kinetic Resolution of α-Thionitriles', Chemistry - A European Journal, vol. 26, no. 46, pp. 10422-10426. https://doi.org/10.1002/chem.202001108

APA

Lauder, K., Anselmi, S., Finnigan, J. D., Qi, Y., Charnock, S. J., & Castagnolo, D. (2020). Enantioselective Synthesis of α-Thiocarboxylic Acids by Nitrilase Biocatalysed Dynamic Kinetic Resolution of α-Thionitriles. Chemistry - A European Journal, 26(46), 10422-10426. https://doi.org/10.1002/chem.202001108

Vancouver

Lauder K, Anselmi S, Finnigan JD, Qi Y, Charnock SJ, Castagnolo D. Enantioselective Synthesis of α-Thiocarboxylic Acids by Nitrilase Biocatalysed Dynamic Kinetic Resolution of α-Thionitriles. Chemistry - A European Journal. 2020 Aug 17;26(46):10422-10426. https://doi.org/10.1002/chem.202001108

Author

Lauder, Kate ; Anselmi, Silvia ; Finnigan, James D. ; Qi, Yuyin ; Charnock, Simon J. ; Castagnolo, Daniele. / Enantioselective Synthesis of α-Thiocarboxylic Acids by Nitrilase Biocatalysed Dynamic Kinetic Resolution of α-Thionitriles. In: Chemistry - A European Journal. 2020 ; Vol. 26, No. 46. pp. 10422-10426.

Bibtex Download

@article{cc73a626e4ea47e0a7deabf3b4075380,
title = "Enantioselective Synthesis of α-Thiocarboxylic Acids by Nitrilase Biocatalysed Dynamic Kinetic Resolution of α-Thionitriles",
abstract = "The enantioselective synthesis of α-thiocarboxylic acids by biocatalytic dynamic kinetic resolution (DKR) of nitrile precursors exploiting nitrilase enzymes is described. A panel of 35 nitrilase biocatalysts were screened and enzymes Nit27 and Nit34 were found to catalyse the DKR of racemic α-thionitriles under mild conditions, affording the corresponding carboxylic acids with high conversions and good-to-excellent ee. The ammonia produced in situ during the biocatalytic transformation favours the racemization of the nitrile enantiomers and, in turn, the DKR without the need of any external additive base.",
keywords = "biocatalysis, dynamic kinetic resolution, nitrilase, thiocarboxylic acid, thionitrile",
author = "Kate Lauder and Silvia Anselmi and Finnigan, {James D.} and Yuyin Qi and Charnock, {Simon J.} and Daniele Castagnolo",
year = "2020",
month = aug,
day = "17",
doi = "10.1002/chem.202001108",
language = "English",
volume = "26",
pages = "10422--10426",
journal = "Chemistry (Weinheim an der Bergstrasse, Germany)",
issn = "0947-6539",
number = "46",

}

RIS (suitable for import to EndNote) Download

TY - JOUR

T1 - Enantioselective Synthesis of α-Thiocarboxylic Acids by Nitrilase Biocatalysed Dynamic Kinetic Resolution of α-Thionitriles

AU - Lauder, Kate

AU - Anselmi, Silvia

AU - Finnigan, James D.

AU - Qi, Yuyin

AU - Charnock, Simon J.

AU - Castagnolo, Daniele

PY - 2020/8/17

Y1 - 2020/8/17

N2 - The enantioselective synthesis of α-thiocarboxylic acids by biocatalytic dynamic kinetic resolution (DKR) of nitrile precursors exploiting nitrilase enzymes is described. A panel of 35 nitrilase biocatalysts were screened and enzymes Nit27 and Nit34 were found to catalyse the DKR of racemic α-thionitriles under mild conditions, affording the corresponding carboxylic acids with high conversions and good-to-excellent ee. The ammonia produced in situ during the biocatalytic transformation favours the racemization of the nitrile enantiomers and, in turn, the DKR without the need of any external additive base.

AB - The enantioselective synthesis of α-thiocarboxylic acids by biocatalytic dynamic kinetic resolution (DKR) of nitrile precursors exploiting nitrilase enzymes is described. A panel of 35 nitrilase biocatalysts were screened and enzymes Nit27 and Nit34 were found to catalyse the DKR of racemic α-thionitriles under mild conditions, affording the corresponding carboxylic acids with high conversions and good-to-excellent ee. The ammonia produced in situ during the biocatalytic transformation favours the racemization of the nitrile enantiomers and, in turn, the DKR without the need of any external additive base.

KW - biocatalysis

KW - dynamic kinetic resolution

KW - nitrilase

KW - thiocarboxylic acid

KW - thionitrile

UR - http://www.scopus.com/inward/record.url?scp=85088126253&partnerID=8YFLogxK

U2 - 10.1002/chem.202001108

DO - 10.1002/chem.202001108

M3 - Article

AN - SCOPUS:85088126253

VL - 26

SP - 10422

EP - 10426

JO - Chemistry (Weinheim an der Bergstrasse, Germany)

JF - Chemistry (Weinheim an der Bergstrasse, Germany)

SN - 0947-6539

IS - 46

ER -

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