KEGG   ENZYME: 2.2.1.12Help
Entry
EC 2.2.1.12                 Enzyme                                 

Name
3-acetyloctanal synthase;
pigD (gene name)
Class
Transferases;
Transferring aldehyde or ketonic groups;
Transketolases and transaldolases
BRITE hierarchy
Sysname
pyruvate:(E)-oct-2-enal acetaldehydetransferase (decarboxylating)
Reaction(IUBMB)
pyruvate + (E)-oct-2-enal = (S)-3-acetyloctanal + CO2 [RN:R11141]
Reaction(KEGG)
Substrate
pyruvate [CPD:C00022];
(E)-oct-2-enal [CPD:C21138]
Product
(S)-3-acetyloctanal [CPD:C21139];
CO2 [CPD:C00011]
Comment
Requires thiamine diphosphate. The enzyme, characterized from the bacterium Serratia marcescens, participates in the biosynthesis of the antibiotic prodigiosin. The enzyme decarboxylates pyruvate, followed by attack of the resulting two-carbon fragment on (E)-oct-2-enal, resulting in a Stetter reaction. In vitro the enzyme can act on a number of alpha,beta-unsaturated carbonyl compounds, including aldehydes and ketones, and can catalyse both 1-2 and 1-4 carboligations depending on the substrate.
History
EC 2.2.1.12 created 2014
Reference
1  [PMID:15853884]
  Authors
Williamson NR, Simonsen HT, Ahmed RA, Goldet G, Slater H, Woodley L, Leeper FJ, Salmond GP
  Title
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.
  Journal
Mol. Microbiol. 56 (2005) 971-89.
Reference
2  [PMID:20669204]
  Authors
Dresen C, Richter M, Pohl M, Ludeke S, Muller M
  Title
The enzymatic asymmetric conjugate umpolung reaction.
  Journal
Angew. Chem. Int. Ed. Engl. 49 (2010) 6600-3.
Reference
3  [PMID:24957249]
  Authors
Kasparyan E, Richter M, Dresen C, Walter LS, Fuchs G, Leeper FJ, Wacker T, Andrade SL, Kolter G, Pohl M, Muller M
  Title
Asymmetric Stetter reactions catalyzed by thiamine diphosphate-dependent enzymes.
  Journal
Appl. Microbiol. Biotechnol. 98 (2014) 9681-90.
Other DBs
ExplorEnz - The Enzyme Database: 
IUBMB Enzyme Nomenclature: 
ExPASy - ENZYME nomenclature database: 
BRENDA, the Enzyme Database: 

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