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Exploration of Aldol Reactions Catalyzed by Stereoselective Pyruvate Aldolases with 2‐Oxobutyric Acid as Nucleophile
Author(s) -
Laurent V.,
Uzel A.,
Hélaine V.,
Nauton L.,
Traïkia M.,
Gefflaut T.,
Salanoubat M.,
de Berardinis V.,
Lemaire M.,
GuérardHélaine C.
Publication year - 2019
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201900128
Subject(s) - aldol reaction , chemistry , stereoselectivity , nucleophile , stereochemistry , adduct , substrate (aquarium) , catalysis , organic chemistry , oceanography , geology
Pyruvate aldolases from Pfam family PF03328, recently described to be able to use hydroxypyruvic acid as nucleophile substrate, were shown to also catalyse aldol adducts formation from 2‐oxobutyric acid. A 1 H NMR‐based assay was used to screen 21 aldolases for their activity towards 2‐oxobutyric acid and to predict their stereoselectivity at position 3 of the aldol adducts. The best biocatalysts were then proved to be strictly (3 S ) ‐ selective. Contrary to known enzymes from this family that are seldom stereoselective at position 4, three aldolases were highlighted as allowing a selective access to (3 S ,4 R ) or (3 S ,4 S ) aldols. Seven 3‐deoxy‐3‐methylulosonic acids never described before were finally prepared and isolated with good yields and stereoselectivities.