Information on EC 1.14.21.9 - mycocyclosin synthase

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The expected taxonomic range for this enzyme is: Mycobacterium tuberculosis

EC NUMBER
COMMENTARY hide
1.14.21.9
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RECOMMENDED NAME
GeneOntology No.
mycocyclosin synthase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
cyclo(L-tyrosyl-L-tyrosyl) + NADPH + H+ + O2 = mycocyclosin + NADP+ + 2 H2O
show the reaction diagram
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
mycocyclosin biosynthesis
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tyrosine metabolism
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SYSTEMATIC NAME
IUBMB Comments
cyclo(L-tyrosyl-L-tyrosyl),NADPH:oxygen oxidoreductase (diarylbridge-forming)
A heme-thiolate (P-450) enzyme from the bacterium Mycobacterium tuberculosis catalysing an oxidative reaction that does not incorporate oxygen into the product.
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
physiological function
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(3S,6S)-3,6-bis(4-hydroxybenzyl)piperazin-2-one + NADPH + H+ + O2
?
show the reaction diagram
cyclo(L-tyrosyl-L-phenylalanyl) + NADPH + H+ + O2
?
show the reaction diagram
cyclo(L-tyrosyl-L-tryptophanyl) + NADPH + H+ + O2
?
show the reaction diagram
cyclo(L-tyrosyl-L-tyrosyl) + NADPH + H+ + O2
mycocyclosin + NADP+ + H2O
show the reaction diagram
cyclo-(L-tyrosyl-DOPA) + NADPH + H+ + O2
?
show the reaction diagram
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transformation of cyclo-(L-tyrosyl-DOPA) by CYP121 is very slow, 91% of the compound remains after 1 h of incubation with CYP121
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?
additional information
?
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
cyclo(L-tyrosyl-L-tyrosyl) + NADPH + H+ + O2
mycocyclosin + NADP+ + H2O
show the reaction diagram
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
cytochrome P450
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CYP121 is a highly specific cytochrome P450
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INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(3S,6S)-3,6-bis(4-hydroxybenzyl)piperazin-2-one
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2-methylquinolin-6-amine
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3-(1H-1,2,4-triazol-1-ylmethyl)aniline
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4,4'-(1H-1,2,3-triazole-1,4-diyl)diphenol
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4,4'-(1H-1,2,3-triazole-1,5-diyl)diphenol
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4-(1,3-thiazol-5-yl)quinolin-6-amine
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4-(1H-1,2,3-triazol-1-yl)quinolin-6-amine
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4-(1H-1,2,4-triazol-1-yl)phenol
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4-(1H-1,2,4-triazol-1-yl)quinolin-6-amine
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4-(1H-1,2,4-triazol-1-yl)quinoline
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4-(1H-imidazol-1-yl)quinolin-6-amine
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4-(1H-pyrazol-1-yl)quinolin-6-amine
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4-(4-phenoxy-1H-pyrazol-3-yl)benzene-1,3-diol
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4-(pyridin-3-yl)quinolin-6-amine
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4-oxo-4,5,6,7-tetrahydro-1-benzofuran-3-carboxylic acid
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4-[4-(4-fluorophenyl)-1H-pyrazol-3-yl]benzene-1,3-diol
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4-[4-(4-methoxyphenyl)-1H-pyrazol-3-yl]benzene-1,3-diol
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6-nitro-4-(1H-1,2,4-triazol-1-yl)quinoline
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cyclo(L-tyrosyl-L-alanyl)
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cyclo(L-tyrosyl-L-phenylalanyl)
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cyclo(L-tyrosyl-L-tryptophanyl)
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cyclo-(L-tyrosyl-DOPA)
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additional information
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not inhibited by cyclo(L-Tyr-L-Leu) and cyclo(L-Tyr-L-Met)
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PDB
SCOP
CATH
ORGANISM
UNIPROT
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
43126
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x * 43126, calculated from amino acid sequence
43128
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x * 43128, electrospray ionization mass spectrometry
44962
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2 * 44962, calculated from amino acid sequence, CYP121 is a predominantly dimeric protein, with a minor monomeric form present
89940
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nanoelectrospray ionization mass spectrometry
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
homodimer
homohexamer
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
fluconazole-bound CYP121, sitting drop vapor diffusion method, using 20% (w/v) polyethylene glycol 3350 and 0.2 M NaSCN
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in complex with cyclo(L-tyrosyl-L-tyrosyl), sitting drop vapor diffusion method
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ligand-bound enzyme, sitting drop vapor diffusion method, using in 100 mM Na-MES bufferat pH 5.0-5.5 and 1.6-2.2 M (NH4)2SO4, at 6°C
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native enzyme or in complex with iodopyrazole, PtCN, K2PtCl4, or Hg(NO3)2, vapor diffusion method, using 30% (w/v) polyethylene glycol 8000, 0.2 M ammonium sulfate, pH 6.5
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
ammonium sulfate precipitation, phenyl Sepharose column chromatography, Q-Sepharose column chromatography, and hydroxyapatite column chromatography
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ammonium sulfate precipitation, phenyl Sepharose column chromatography, Q-Sepharose column chromatography, and hydroxyapatite resin column chromatography
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli
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expressed in Escherichia coli HMS174 (DE3) cells
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