volume 34 issue 9 pages 108178

Asymmetric synthesis of syn-aryl-(2S,3R)-2-chloro-3-hydroxy esters via an engineered ketoreductase-catalyzed dynamic reductive kinetic resolution

Xiaoping Yue 1
Yitong Li 1
Di Sang 2, 3
Tao Yuan 2, 3
Zedu Huang 2, 3
Fen-Er Chen 1, 2, 3
Publication typeJournal Article
Publication date2023-09-01
scimago Q1
wos Q1
SJR1.677
CiteScore15.7
Impact factor8.9
ISSN10018417, 18785964
General Chemistry
Abstract
We report here a generic, green synthesis of 17 valuable syn-aryl-(2S,3R)-2-chloro-3-hydroxy esters (syn-(2S,3R)-1) in 73%-99% isolated yields along with 6.1:1-83:1 dr and 31%->99% ee, through dynamic reductive kinetic resolution of racemic aryl α-chloro β-keto esters (2) catalyzed by an engineered ketoreductase which was obtained via epPCR-based directed evolution. The hectogram scale synthesis of syn-(2S,3R)-1b at a substrate concentration of 120 g/L showcased the application potential of the biocatalytic method developed presently.
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GOST Copy
Yue X. et al. Asymmetric synthesis of syn-aryl-(2S,3R)-2-chloro-3-hydroxy esters via an engineered ketoreductase-catalyzed dynamic reductive kinetic resolution // Chinese Chemical Letters. 2023. Vol. 34. No. 9. p. 108178.
GOST all authors (up to 50) Copy
Yue X., Li Y., Sang D., Yuan T., Huang Z., Chen F. Asymmetric synthesis of syn-aryl-(2S,3R)-2-chloro-3-hydroxy esters via an engineered ketoreductase-catalyzed dynamic reductive kinetic resolution // Chinese Chemical Letters. 2023. Vol. 34. No. 9. p. 108178.
RIS |
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RIS Copy
TY - JOUR
DO - 10.1016/j.cclet.2023.108178
UR - https://doi.org/10.1016/j.cclet.2023.108178
TI - Asymmetric synthesis of syn-aryl-(2S,3R)-2-chloro-3-hydroxy esters via an engineered ketoreductase-catalyzed dynamic reductive kinetic resolution
T2 - Chinese Chemical Letters
AU - Yue, Xiaoping
AU - Li, Yitong
AU - Sang, Di
AU - Yuan, Tao
AU - Huang, Zedu
AU - Chen, Fen-Er
PY - 2023
DA - 2023/09/01
PB - Elsevier
SP - 108178
IS - 9
VL - 34
SN - 1001-8417
SN - 1878-5964
ER -
BibTex |
Cite this
BibTex (up to 50 authors) Copy
@article{2023_Yue,
author = {Xiaoping Yue and Yitong Li and Di Sang and Tao Yuan and Zedu Huang and Fen-Er Chen},
title = {Asymmetric synthesis of syn-aryl-(2S,3R)-2-chloro-3-hydroxy esters via an engineered ketoreductase-catalyzed dynamic reductive kinetic resolution},
journal = {Chinese Chemical Letters},
year = {2023},
volume = {34},
publisher = {Elsevier},
month = {sep},
url = {https://doi.org/10.1016/j.cclet.2023.108178},
number = {9},
pages = {108178},
doi = {10.1016/j.cclet.2023.108178}
}
MLA
Cite this
MLA Copy
Yue, Xiaoping, et al. “Asymmetric synthesis of syn-aryl-(2S,3R)-2-chloro-3-hydroxy esters via an engineered ketoreductase-catalyzed dynamic reductive kinetic resolution.” Chinese Chemical Letters, vol. 34, no. 9, Sep. 2023, p. 108178. https://doi.org/10.1016/j.cclet.2023.108178.