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IUBMB Comments The enzyme catalyses the first committed step in the biosynthesis of γ-butyrolactone, as well as 2-alkyl-4-hydroxymethylfuran-3-carboxylate (methylenomycin furan) autoregulators that control secondary metabolism and morphological development in Streptomyces bacteria.
The expected taxonomic range for this enzyme is: Streptomyces
Reaction Schemes
+
=
a (4-alkanoyl-5-oxo-2H-furan-3-yl)methyl phosphate
+
+
Synonyms 2-oxo-3-(phosphooxy)propyl 3-oxoalkanoate synthase, afsA , barX , mmfL , scbA , more
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2-oxo-3-(phosphooxy)propyl 3-oxoalkanoate synthase
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afsA
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barX
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scbA
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a 2-oxo-3-(phosphooxy)propyl 3-oxoalkanoate = a (4-alkanoyl-5-oxo-2H-furan-3-yl)methyl phosphate + H2O
(1b), spontaneous
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a 3-oxoacyl-[acyl-carrier protein] + glycerone phosphate = a (4-alkanoyl-5-oxo-2H-furan-3-yl)methyl phosphate + H2O + a holo-[acyl-carrier protein]
overall reaction
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a 3-oxoacyl-[acyl-carrier protein] + glycerone phosphate = a 2-oxo-3-(phosphooxy)propyl 3-oxoalkanoate + a holo-[acyl-carrier protein]
(1a)
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MetaCyc
A-factor gamma-butyrolactone biosynthesis, IM-2 type gamma-butyrolactones biosynthesis, virginiae butanolide type gamma-butyrolactones biosynthesis
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3-oxoacyl-[acyl-carrier protein]:glycerone phosphate 3-oxoacyltransferase
The enzyme catalyses the first committed step in the biosynthesis of gamma-butyrolactone, as well as 2-alkyl-4-hydroxymethylfuran-3-carboxylate (methylenomycin furan) autoregulators that control secondary metabolism and morphological development in Streptomyces bacteria.
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a medium-chain 3-oxoacyl-[acyl-carrier protein] + glycerone phosphate
2-oxo-3-(phosphooxy)propyl 3-oxoalkanoate + a holo-[acyl-carrier protein]
a medium-chain 3-oxoacyl-[acyl-carrier protein] + glycerone phosphate
2-oxo-3-(phosphooxy)propyl 3-oxoalkanoate + a holo-[acyl-carrier protein]
Substrates: the enzyme is involved in biosynthesis of gamma-butyrolactone Products: -
?
a medium-chain 3-oxoacyl-[acyl-carrier protein] + glycerone phosphate
2-oxo-3-(phosphooxy)propyl 3-oxoalkanoate + a holo-[acyl-carrier protein]
Substrates: - Products: -
?
a medium-chain 3-oxoacyl-[acyl-carrier protein] + glycerone phosphate
2-oxo-3-(phosphooxy)propyl 3-oxoalkanoate + a holo-[acyl-carrier protein]
Substrates: key enzyme for A-factor (2-isocapryloyl-3R-hydroxymethyl-y-butyrolactone) biosynthesis Products: -
?
a medium-chain 3-oxoacyl-[acyl-carrier protein] + glycerone phosphate
2-oxo-3-(phosphooxy)propyl 3-oxoalkanoate + a holo-[acyl-carrier protein]
Substrates: AfsA is the key enzyme for A factor biosynthesis Products: -
?
a medium-chain 3-oxoacyl-[acyl-carrier protein] + glycerone phosphate
2-oxo-3-(phosphooxy)propyl 3-oxoalkanoate + a holo-[acyl-carrier protein]
Substrates: - Products: -
?
a medium-chain 3-oxoacyl-[acyl-carrier protein] + glycerone phosphate
2-oxo-3-(phosphooxy)propyl 3-oxoalkanoate + a holo-[acyl-carrier protein]
Substrates: AfsA is the key enzyme for A factor biosynthesis Products: -
?
a medium-chain 3-oxoacyl-[acyl-carrier protein] + glycerone phosphate
2-oxo-3-(phosphooxy)propyl 3-oxoalkanoate + a holo-[acyl-carrier protein]
Substrates: - Products: -
?
a medium-chain 3-oxoacyl-[acyl-carrier protein] + glycerone phosphate
2-oxo-3-(phosphooxy)propyl 3-oxoalkanoate + a holo-[acyl-carrier protein]
Substrates: the enzyme is involved in biosynthesis of the gamma-butyrolactone autoregulator in Streptomyces virginiae Products: -
?
a medium-chain 3-oxoacyl-[acyl-carrier protein] + glycerone phosphate
2-oxo-3-(phosphooxy)propyl 3-oxoalkanoate + a holo-[acyl-carrier protein]
Substrates: the enzyme is involved in biosynthesis of gamma-butyrolactone Products: -
?
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a medium-chain 3-oxoacyl-[acyl-carrier protein] + glycerone phosphate
2-oxo-3-(phosphooxy)propyl 3-oxoalkanoate + a holo-[acyl-carrier protein]
a medium-chain 3-oxoacyl-[acyl-carrier protein] + glycerone phosphate
2-oxo-3-(phosphooxy)propyl 3-oxoalkanoate + a holo-[acyl-carrier protein]
Substrates: the enzyme is involved in biosynthesis of gamma-butyrolactone Products: -
?
a medium-chain 3-oxoacyl-[acyl-carrier protein] + glycerone phosphate
2-oxo-3-(phosphooxy)propyl 3-oxoalkanoate + a holo-[acyl-carrier protein]
Substrates: key enzyme for A-factor (2-isocapryloyl-3R-hydroxymethyl-y-butyrolactone) biosynthesis Products: -
?
a medium-chain 3-oxoacyl-[acyl-carrier protein] + glycerone phosphate
2-oxo-3-(phosphooxy)propyl 3-oxoalkanoate + a holo-[acyl-carrier protein]
Substrates: AfsA is the key enzyme for A factor biosynthesis Products: -
?
a medium-chain 3-oxoacyl-[acyl-carrier protein] + glycerone phosphate
2-oxo-3-(phosphooxy)propyl 3-oxoalkanoate + a holo-[acyl-carrier protein]
Substrates: AfsA is the key enzyme for A factor biosynthesis Products: -
?
a medium-chain 3-oxoacyl-[acyl-carrier protein] + glycerone phosphate
2-oxo-3-(phosphooxy)propyl 3-oxoalkanoate + a holo-[acyl-carrier protein]
Substrates: the enzyme is involved in biosynthesis of the gamma-butyrolactone autoregulator in Streptomyces virginiae Products: -
?
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additional information
no metals are required for the activity
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additional information
EDTA (5 mM) has no effect on the reaction
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0.2046
glycerone phosphate
pH 7.5, 15°C
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2
glycerone phosphate
pH 7.5, 15°C
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6.5 - 7.5
Trisx01HCl buffer
7 - 8
sodium phosphate-citrate buffer
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15 - 30
at 30°C, the activity decreases to 32% of that measured at 15°C, and almost no activity is detected at 35°C
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UniProt
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SwissProt
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SwissProt
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UniProt
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Highest Expressing Human Cell Lines
Filter by:
Cell Line Links
Gene Links
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additional information
the enzyme is involved in biosynthesis of gamma-butyrolactone
metabolism
key enzyme for A-factor (2-isocapryloyl-3R-hydroxymethyl-y-butyrolactone) biosynthesis
metabolism
the enzyme is involved in biosynthesis of the gamma-butyrolactone autoregulator in Streptomyces virginiae
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AFSA_STRGG
Streptomyces griseus subsp. griseus (strain JCM 4626 / CBS 651.72 / NBRC 13350 / KCC S-0626 / ISP 5235)
314
0
34041
Swiss-Prot
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BARX_STRVG
294
0
32379
Swiss-Prot
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AFSA_STRGR
301
0
32706
Swiss-Prot
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SCBA_STRCO
Streptomyces coelicolor (strain ATCC BAA-471 / A3(2) / M145)
314
0
33747
Swiss-Prot
-
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monomer
1 * 37700, SDS-PAGE
monomer
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1 * 37700, SDS-PAGE
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expression in Escherichia coli
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Kato, J.; Funa, N.; Watanabe, H.; Ohnishi, Y.; Horinouchi, S.
Biosynthesis of gamma-butyrolactone autoregulators that switch on secondary metabolism and morphological development in Streptomyces
Proc. Natl. Acad. Sci. USA
104
2378-2383
2007
Streptomyces griseus (P18394), Streptomyces griseus IFO13350 (P18394)
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brenda
Horinouchi, S.; Suzuki, H.; Nishiyama, M.; Beppu, T.
Nucleotide sequence and transcriptional analysis of the Streptomyces griseus gene (afsA) responsible for A-factor biosynthesis
J. Bacteriol.
171
1206-1210
1989
Streptomyces griseus (P18394)
brenda
Hsiao, N.; Sding, J.; Linke, D.; Lange, C.; Hertweck, C.; Wohlleben, W.; Takano, E.
ScbA from Streptomyces coelicolor A3(2) has homology to fatty acid synthases and is able to synthesize gamma-butyrolactones
Microbiology
153
1394-1404
2007
Streptomyces coelicolor (Q7AKF0)
brenda
Lee, Y.; Kitani, S.; Nihira, T.
Null mutation analysis of an afsA-family gene, barX, that is involved in biosynthesis of the gamma-butyrolactone autoregulator in Streptomyces virginiae
Microbiology
156
206-210
2010
Streptomyces virginiae (O24738)
brenda
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