(S)-Selective MenD variants from Escherichia coli provide access to new functionalized chiral α-hydroxy ketones.
We report the first rationally designed (S)-selective MenD from E. coli for the synthesis of functionalized α-hydroxy ketones. By mutation of two amino acids in the active site stereoselectivity of the (R)-selective EcMenD (ee > 93%) was inverted giving access to (S)-5-hydroxy-4-oxo-5-phenylpentanoate derivatives with stereoselectivities up to 97% ee.
IBG-1: Biotechnology, Forschungszentrum Jülich GmbH, Leo-Brandt-Str. 1, 52425 Jülich, Germany.
Robert
R
Westphal
Simon
S
Waltzer
Ursula
U
Mackfeld
Michael
M
Widmann
Jürgen
J
Pleiss
Maryam
M
Beigi
Michael
M
Müller
Dörte
D
Rother
Martina
M
Pohl
D000447:Aldehydes / Q000737:chemistry; D055162:Biocatalysis; D020134:Catalytic Domain; D004926:Escherichia coli / Q000378:metabolism*; D029968:Escherichia coli Proteins / Q000235:genetics / Q000378:metabolism*; D007659:Ketones / Q000737:chemistry / Q000378:metabolism*; D009154:Mutation; D011771:Pyruvate Oxidase / Q000235:genetics / Q000378:metabolism*; D013237:Stereoisomerism
D000447:Aldehydes; D029968:Escherichia coli Proteins; D007659:Ketones; C534108:2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexadiene-1-carboxylate synthase, E coli; D011771:Pyruvate Oxidase