ExplorEnz: EC 2.3.1.277

Your query returned 1 entry. Printable version

2.3.1.277

Accepted name:

phosphorylated butenolide synthase

Reaction:

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)
(1a) a 3-oxoacyl-[acyl-carrier protein] + glycerone phosphate = a 2-oxo-3-(phosphooxy)propyl 3-oxoalkanoate + a holo-[acyl-carrier protein]
(1b) a 2-oxo-3-(phosphooxy)propyl 3-oxoalkanoate = a (4-alkanoyl-5-oxo-2H-furan-3-yl)methyl phosphate + H₂O (spontaneous)

Glossary:

glycerone phosphate = dihydroxyacetone phosphate = 3-hydroxy-2-oxopropyl phosphate

Other name(s):

2-oxo-3-(phosphooxy)propyl 3-oxoalkanoate synthase; afsA (gene name); scbA (gene name); barX (gene name); mmfL (gene name)

Systematic name:

3-oxoacyl-[acyl-carrier protein]:glycerone phosphate 3-oxoacyltransferase

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.

Links to other databases:

BRENDA, EXPASY, Gene, KEGG, MetaCyc

References:

1.	Horinouchi, S., Suzuki, H., Nishiyama, M. and Beppu, T. Nucleotide sequence and transcriptional analysis of the Streptomyces griseus gene (afsA) responsible for A-factor biosynthesis. J. Bacteriol. 171 (1989) 1206–1210. [PMID: 2492509]
2.	Kato, J.Y., Funa, N., Watanabe, H., Ohnishi, Y. and Horinouchi, S. Biosynthesis of γ-butyrolactone autoregulators that switch on secondary metabolism and morphological development in Streptomyces. Proc. Natl. Acad. Sci. USA 104 (2007) 2378–2383. [DOI] [PMID: 17277085]
3.	Hsiao, N.H., Soding, J., Linke, D., Lange, C., Hertweck, C., Wohlleben, W. and Takano, E. ScbA from Streptomyces coelicolor A3(2) has homology to fatty acid synthases and is able to synthesize γ-butyrolactones. Microbiology 153 (2007) 1394–1404. [PMID: 17464053]
4.	Lee, Y.J., Kitani, S. and Nihira, T. Null mutation analysis of an afsA-family gene, barX, that is involved in biosynthesis of the γ-butyrolactone autoregulator in Streptomyces virginiae. Microbiology 156 (2010) 206–210. [PMID: 19778967]
5.	Corre, C., Haynes, S.W., Malet, N., Song, L. and Challis, G.L. A butenolide intermediate in methylenomycin furan biosynthesis is implied by incorporation of stereospecifically ¹³C-labelled glycerols. Chem. Commun. (Camb.) 46 (2010) 4079–4081. [DOI] [PMID: 20358097]
6.	Zhou, S., Malet, N.R., Song, L., Corre, C. and Challis, G.L. MmfL catalyses formation of a phosphorylated butenolide intermediate in methylenomycin furan biosynthesis. Chem. Commun. (Camb.) 56 (2020) 14443–14446. [DOI] [PMID: 33146163]

[EC 2.3.1.277 created 2018, modified 2024]