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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 enzyme appears in viruses and cellular organisms
Synonyms
methyl nogalonate cyclase, SnoaL,
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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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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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SNOAL_STRNO
134
0
15505
Swiss-Prot
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A0A7Y9XH04_9ACTN
144
0
16736
TrEMBL
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A0A7W4ZTC7_9ACTN
145
0
16721
TrEMBL
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A0A7X0KE78_9ACTN
144
0
16469
TrEMBL
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A0A7W9LZV1_9PSEU
145
0
16740
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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