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IUBMB Comments The enzyme, characterized from the bacterium Streptomyces nogalater, is involved in the biosynthesis of the aromatic polyketide nogalamycin.
The expected taxonomic range for this enzyme is: Streptomyces nogalater
Synonyms
snoal, nogalonic acid methyl ester cyclase,
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methyl nogalonate cyclase
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SnoaL
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nogalaviketone = methyl nogalonate
nogalaviketone = methyl nogalonate
the mechanism of the intramolecular aldol condensation catalysed by the enzyme is different from that of the classical aldolases, which employ covalent Schiff base formation or a metal ion cofactor. The invariant residue Asp121 acts as an acid/base catalyst during the reaction. Stabilisation of the enol(ate) intermediate is mainly achieved by the delocalisation of the electron pair over the extended p system of the substrate
nogalaviketone = methyl nogalonate
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methyl nogalonate lyase (cyclizing)
The enzyme, characterized from the bacterium Streptomyces nogalater, is involved in the biosynthesis of the aromatic polyketide nogalamycin.
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methyl nogalonate
nogalaviketone
nogalaviketone
methyl nogalonate
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methyl nogalonate
nogalaviketone
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methyl nogalonate
nogalaviketone
the mechanism of the intramolecular aldol condensation catalysed by the enzyme is different from that of the classical aldolases, which employ covalent Schiff base formation or a metal ion cofactor. The invariant residue Asp121 acts as an acid/base catalyst during the reaction. Stabilisation of the enol(ate) intermediate is mainly achieved by the delocalisation of the electron pair over the extended p system of the substrate
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?
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methyl nogalonate
nogalaviketone
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nogalaviketone
methyl nogalonate
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UniProt
brenda
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brenda
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Q9RN59_STRNO
134
0
15505
TrEMBL
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20471
4 * 20471, calculated from sequence
20472
4 * 20472, mass spectrometry
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tetramer
4 * 20471, calculated from sequence
tetramer
4 * 20472, mass spectrometry
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crystal structure of the enzyme with a bound product, determined to 1.35 A resolution
hanging-drop vapour-diffusion method. Crystals of a complex of the enzyme with the substrate nogalonic acid methyl ester, obtained using PEG 4000 as precipitant. The crystals are orthorhombic, space group I222, with unit-cell parameters a = 69.1, b = 72.0, c = 65.4 A. They diffract to 1.35 A resolution using synchrotron radiation
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D121A
inactive mutant enzyme
D121N
mutant enzyme forms insoluble inclusion bodies
F15Y
mutant enzyme shows 5% of the activity compared to the wild-type enzyme
Q105A
mutant enzyme shows 16% of the activity compared to the wild-type enzyme
Q105E
mutant enzyme forms insoluble inclusion bodies
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expressed in Streptomyces coeruleobidus strain DM
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expression in Escherichia coli
produced in Escherichia coli with an N-terminal 6*His tag
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Sultana, A.; Kallio, P.; Jansson, A.; Niemi, J.; Mäntsälä, P.; Schneider, G.
Crystallization and preliminary crystallographic data of SnoaL, a polyketide cyclase in nogalamycin biosynthesis
Acta Crystallogr. Sect. D
60
1118-1120
2004
Streptomyces nogalater (Q9RN59)
brenda
Torkkell, S.; Kunnari. T.; Palmu, K.; Hakala, J.; Mäntsälä, P.; Ylihonko, K.
Identification of a cyclase gene dictating the C-9 stereochemistry of anthracyclines from Streptomyces nogalater
Antimicrob. Agents Chemother.
44
396-399
2000
Streptomyces nogalater (Q9RN59), Streptomyces nogalater
brenda
Sultana, A.; Kallio, P.; Jansson, A.; Wang, J.S.; Niemi, J.; Mäntsälä, P.; Schneider, G.
Structure of the polyketide cyclase SnoaL reveals a novel mechanism for enzymatic aldol condensation
EMBO J.
23
1911-1921
2004
Streptomyces nogalater (Q9RN59)
brenda
Yuan, T.; Xie, L.; Zhu, B.; Hu, Y.
Bioconversion of deoxysugar moieties to the biosynthetic intermediates of daunorubicin in an engineered strain of Streptomyces coeruleobidus
Biotechnol. Lett.
36
1809-1818
2014
Streptomyces nogalater
brenda
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5.5.1.26 nogalonic acid methyl ester cyclase
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