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2-oxobutanoate + (3E)-4-(4-chlorophenyl)but-3-en-2-one
?
-
-
-
?
pyruvate + (2E)-1,3-diphenylprop-2-en-1-one
(3R)-1,3-diphenylpentane-1,4-dione + CO2
the PigD-catalyzed reaction yields 3% 1,4-carboligation product, with an enantiomeric excess above 99%
-
-
?
pyruvate + (2E)-3-(2-hydroxyphenyl)-1-phenylprop-2-en-1-one
(3R)-3-(2-hydroxyphenyl)-1-phenylpentane-1,4-dione + CO2
the PigD-catalyzed reaction yields 39% 1,4-carboligation product, with an enantiomeric excess above 99%
-
-
?
pyruvate + (2E)-3-(4-methoxyphenyl)-1-phenylprop-2-en-1-one
(3R)-3-(4-methoxyphenyl)-1-phenylpentane-1,4-dione + CO2
-
-
-
?
pyruvate + (3E)-4-(4-chlorophenyl)but-3-en-2-one
(3R)-3-(4-chlorophenyl)hexane-2,5-dione + CO2
pyruvate + (3E)-4-(4-hydroxy-3-methoxyphenyl)but-3-en-2-one
(3R)-3-(4-hydroxy-3-methoxyphenyl)hexane-2,5-dione + CO2
-
-
-
?
pyruvate + (3E)-4-(furan-2-yl)but-3-en-2-one
(3R)-3-(furan-2-yl)hexane-2,5-dione + CO2
10% conversion
-
-
?
pyruvate + (3E)-4-(furan-2-yl)but-3-en-2-one
3-(furan-2-yl)hexane-2,5-dione + CO2
11% conversion
-
-
?
pyruvate + (3E)-4-(thiophen-2-yl)but-3-en-2-one
(3S)-3-(thiophen-2-yl)hexane-2,5-dione + CO2
15% conversion
-
-
?
pyruvate + (3E)-4-phenylbut-3-en-2-one
(3R)-3-phenylhexane-2,5-dione + CO2
pyruvate + (3E)-dec-3-en-2-one
(3S)-3-hexylhexane-2,5-dione + CO2
the PigD-catalyzed reaction yields 30% 1,4-carboligation product, with an enantiomeric excess above 99%
-
-
?
pyruvate + (3E)-non-3-en-2-one
(3S)-3-pentylhexane-2,5-dione + CO2
pyruvate + (E)-oct-2-enal
(S)-3-acetyloctanal + CO2
pyruvate + 3-phenylbut-3-en-2-one
(3R)-3-phenylhexane-2,5-dione + CO2
-
-
-
?
pyruvate + but-3-en-2-one
hexane-2,5-dione + CO2
8% conversion
-
-
?
pyruvate + S-[2-(acetylamino)ethyl] (2E)-oct-2-enethioate
S-[2-(acetylamino)ethyl] (2E)-oct-2-enethioate + CO2
highest conversion of all tested substrates into the 1,4-addition product
-
-
?
pyruvate + S-[2-(acetylamino)ethyl] (2E)-oct-2-enethioate
S-[2-(acetylamino)ethyl] 3-acetyloctanethioate + CO2
75% conversion
-
-
?
additional information
?
-
PigD catalyzes 1,2-additions using 2-oxoacids as donor substrates and aldehydes as acceptors. In the case of ketones as acceptors PigD catalyzes the 1,4-addition. Although pyruvate is the preferred donor substrate, 2-oxobutanoate is also employed using (E)-4-(4-chlorophenyl)-but-3-en-2-one as an acceptor
-
-
?
pyruvate + (3E)-4-(4-chlorophenyl)but-3-en-2-one
(3R)-3-(4-chlorophenyl)hexane-2,5-dione + CO2
39% conversion. (3R)-3-(4-Chlorophenyl)hexane-2,5-dione is produced with 75% enantiomeric excess
-
-
?
pyruvate + (3E)-4-(4-chlorophenyl)but-3-en-2-one
(3R)-3-(4-chlorophenyl)hexane-2,5-dione + CO2
the PigD-catalyzed reaction yields 13% 1,4-carboligation product, with an enantiomeric excess above 99%
-
-
?
pyruvate + (3E)-4-phenylbut-3-en-2-one
(3R)-3-phenylhexane-2,5-dione + CO2
10% conversion. (3R)-3-Phenylhexane-2,5-dione is produced with 82-95% enantiomeric excess
-
-
?
pyruvate + (3E)-4-phenylbut-3-en-2-one
(3R)-3-phenylhexane-2,5-dione + CO2
the PigD-catalyzed reaction yields 7% 1,4-carboligation product, with an enantiomeric excess above 95%
-
-
?
pyruvate + (3E)-non-3-en-2-one
(3S)-3-pentylhexane-2,5-dione + CO2
37% conversion. (3S)-3-pentylhexane-2,5-dione is produced with more than 99% enantiomeric excess
-
-
?
pyruvate + (3E)-non-3-en-2-one
(3S)-3-pentylhexane-2,5-dione + CO2
the PigD-catalyzed reaction yields 38% 1,4-carboligation product, with an enantiomeric excess above 99%
-
-
?
pyruvate + (E)-oct-2-enal
(S)-3-acetyloctanal + CO2
-
-
-
-
?
pyruvate + (E)-oct-2-enal
(S)-3-acetyloctanal + CO2
-
-
-
?
pyruvate + (E)-oct-2-enal
(S)-3-acetyloctanal + CO2
first step in the biosynthesis of the red pigment, prodigiosin
-
-
?
pyruvate + (E)-oct-2-enal
(S)-3-acetyloctanal + CO2
-
-
-
-
?
pyruvate + (E)-oct-2-enal
(S)-3-acetyloctanal + CO2
-
the enzyme participates in the biosynthesis of the antibiotic prodigiosin
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?
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Dresen, C.; Richter, M.; Pohl, M.; Lüdeke, S.; Müller, M.
The enzymatic asymmetric conjugate umpolung reaction
Angew. Chem. Int. Ed. Engl.
49
6600-6603
2010
Serratia marcescens (Q5W251)
brenda
Kasparyan, E.; Richter, M.; Dresen, C.; Walter, L.S.; Fuchs, G.; Leeper, F.J.; Wacker, T.; Andrade, S.L.; Kolter, G.; Pohl, M.; Mueller, M.
Asymmetric Stetter reactions catalyzed by thiamine diphosphate-dependent enzymes
Appl. Microbiol. Biotechnol.
98
9681-9690
2014
Serratia marcescens (Q5W251)
brenda
Williamson, N.R.; Simonsen, H.T.; Ahmed, R.A.; Goldet, G.; Slater, H.; Woodley, L.; Leeper, F.J.; Salmond, G.P.
Biosynthesis of the red antibiotic, prodigiosin, in Serratia: identification of a novel 2-methyl-3-n-amyl-pyrrole (MAP) assembly pathway, definition of the terminal condensing enzyme, and implications for undecylprodigiosin biosynthesis in Streptomyces
Mol. Microbiol.
56
971-989
2005
Serratia sp.
brenda
Mueller, M.; Sprenger, G.A.; Pohl, M.
CC bond formation using ThDP-dependent lyases
Curr. Opin. Chem. Biol.
17
261-270
2013
Serratia marcescens
brenda
2.2.1.12 3-acetyloctanal synthase
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