Synthesis of enantiopure glycidol derivatives via a one-pot two-step enzymatic cascade

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Synthesis of enantiopure glycidol derivatives via a one-pot two-step enzymatic cascade. / Liu, Yu Chang; Liu, Yan; Wu, Zhong Liu.

In: ORGANIC AND BIOMOLECULAR CHEMISTRY, Vol. 13, No. 7, 21.02.2015, p. 2146-2152.

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@article{db340222ce924c6aa31a6a1147745edb,
title = "Synthesis of enantiopure glycidol derivatives via a one-pot two-step enzymatic cascade",
abstract = "Styrene monooxygenase (SMO) can catalyze the kinetic resolution of secondary allylic alcohols to provide enantiopure glycidol derivatives. To overcome the low theoretical yield of kinetic resolution, we designed a one-pot two-step enzymatic cascade using prochiral α,β-unsaturated ketones as the substrates. An S-specific ketoreductase ChKRED03 was screened for the efficient bioreduction of the substrates to provide (S)-allylic alcohols, which underwent SMO-catalyzed epoxidation to achieve glycidol derivatives with contiguous stereogenic centers. Excellent enantioselectivity (ee > 99{\%}) and diastereoselectivity (de > 99{\%}) were achieved for the majority of the substrates, and product yields reached up to >99{\%}. This journal is",
author = "Liu, {Yu Chang} and Yan Liu and Wu, {Zhong Liu}",
year = "2015",
month = "2",
day = "21",
doi = "10.1039/c4ob02186j",
language = "English",
volume = "13",
pages = "2146--2152",
journal = "ORGANIC AND BIOMOLECULAR CHEMISTRY",
issn = "1477-0520",
number = "7",

}

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TY - JOUR

T1 - Synthesis of enantiopure glycidol derivatives via a one-pot two-step enzymatic cascade

AU - Liu, Yu Chang

AU - Liu, Yan

AU - Wu, Zhong Liu

PY - 2015/2/21

Y1 - 2015/2/21

N2 - Styrene monooxygenase (SMO) can catalyze the kinetic resolution of secondary allylic alcohols to provide enantiopure glycidol derivatives. To overcome the low theoretical yield of kinetic resolution, we designed a one-pot two-step enzymatic cascade using prochiral α,β-unsaturated ketones as the substrates. An S-specific ketoreductase ChKRED03 was screened for the efficient bioreduction of the substrates to provide (S)-allylic alcohols, which underwent SMO-catalyzed epoxidation to achieve glycidol derivatives with contiguous stereogenic centers. Excellent enantioselectivity (ee > 99%) and diastereoselectivity (de > 99%) were achieved for the majority of the substrates, and product yields reached up to >99%. This journal is

AB - Styrene monooxygenase (SMO) can catalyze the kinetic resolution of secondary allylic alcohols to provide enantiopure glycidol derivatives. To overcome the low theoretical yield of kinetic resolution, we designed a one-pot two-step enzymatic cascade using prochiral α,β-unsaturated ketones as the substrates. An S-specific ketoreductase ChKRED03 was screened for the efficient bioreduction of the substrates to provide (S)-allylic alcohols, which underwent SMO-catalyzed epoxidation to achieve glycidol derivatives with contiguous stereogenic centers. Excellent enantioselectivity (ee > 99%) and diastereoselectivity (de > 99%) were achieved for the majority of the substrates, and product yields reached up to >99%. This journal is

UR - http://www.scopus.com/inward/record.url?scp=84922662979&partnerID=8YFLogxK

U2 - 10.1039/c4ob02186j

DO - 10.1039/c4ob02186j

M3 - Article

VL - 13

SP - 2146

EP - 2152

JO - ORGANIC AND BIOMOLECULAR CHEMISTRY

JF - ORGANIC AND BIOMOLECULAR CHEMISTRY

SN - 1477-0520

IS - 7

ER -

ID: 14582321