Hydroxynitrile Lyase Isozymes from Prunus communis: Identification, Characterization and Synthetic Applications

Biocatalysts originating from Badamu (Prunus communis) have been applied to catalyze the asymmetric synthesis of (R)‐4‐methylsulfanylmandelonitrile, a key building block of thiamphenicol and florfenicol. Here, four hydroxynitrile lyase (HNL) isozymes from Badamu were cloned and heterologously expres...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2017-04, Vol.359 (7), p.1185-1193
Main Authors: Zheng, Yu‐Cong, Xu, Jian‐He, Wang, Hui, Lin, Guo‐Qiang, Hong, Ran, Yu, Hui‐Lei
Format: Article
Language:English
Subjects:
Alcohols
Aldehydes
Asymmetry
biocatalysis
Biochemistry
Catalysis
characterization
Chemical synthesis
chiral cyanohydrins
Converting
Efficiency
Enzymes
hydrocyanation
hydroxynitrile lyase isozymes
Pichia pastoris
Selectivity
Substrates
Synthesis (chemistry)
Yeast
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Summary:Biocatalysts originating from Badamu (Prunus communis) have been applied to catalyze the asymmetric synthesis of (R)‐4‐methylsulfanylmandelonitrile, a key building block of thiamphenicol and florfenicol. Here, four hydroxynitrile lyase (HNL) isozymes from Badamu were cloned and heterologously expressed in Pichia pastoris. The biochemical properties and catalytic performances of these isozymes were comprehensively explored to evaluate their efficiency and selectivity in asymmetric synthesis. Among then, PcHNL5 was identified with outstanding activity and enantioselectivity in asymmetric hydrocyanation. Under the optimized mild biphasic reaction conditions, seventeen prochiral aromatic aldehydes were converted to valuable chiral cyanohydrins with good yields (up to 94%) and excellent optical purities (up to >99.9% ee), which provide a facile access to numerous chiral amino alcohols, hypoglycemic agents, angiotension converting enzyme (ACE) inhibitors and β‐blockers. This work therefore underlines the importance of discovering the most potent biocatalyst among a group of isozymes for converting unnatural substrates into value‐added products.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201601332