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Information on EC 1.13.12.21 - tetracenomycin-F1 monooxygenase

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EC Tree

1 Oxidoreductases

1.13 Acting on single donors with incorporation of molecular oxygen (oxygenases)

1.13.12 With incorporation of one atom of oxygen (internal monooxygenases or internal mixed-function oxidases)

1.13.12.21 tetracenomycin-F1 monooxygenase

IUBMB Comments

The enzyme is involved in biosynthesis of the anthracycline antibiotic tetracenomycin C by the bacterium Streptomyces glaucescens.

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The expected taxonomic range for this enzyme is: Streptomyces glaucescens

Reaction Schemes

Synonyms

TcmF1 monooxygenase, TmcH, show all synonyms

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SYNONYM

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

TcmF1 monooxygenase

Streptomyces glaucescens

721576

TmcH

Streptomyces glaucescens

722482

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REACTION

REACTION DIAGRAM

COMMENTARY

ORGANISM

UNIPROT

LITERATURE

tetracenomycin F1 + O2 = tetracenomycin D3 + H2O

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PATHWAY SOURCE

PATHWAYS

BRENDA

elloramycin biosynthesis

KEGG

Biosynthesis of antibiotics, Biosynthesis of type II polyketide products

MetaCyc

elloramycin biosynthesis, tetracenomycin C biosynthesis

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SYSTEMATIC NAME

IUBMB Comments

tetracenomycin-F1:oxygen C5-monooxygenase

The enzyme is involved in biosynthesis of the anthracycline antibiotic tetracenomycin C by the bacterium Streptomyces glaucescens.

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SUBSTRATE

PRODUCT

REACTION DIAGRAM

ORGANISM

UNIPROT

COMMENTARY
(Substrate)

LITERATURE
(Substrate)

COMMENTARY
(Product)

LITERATURE
(Product)

Reversibility
r=reversible
ir=irreversible
?=not specified

tetracenomycin F1 + O2

tetracenomycin D3 + H2O

2 entries

tetracenomycin F1 + O2

tetracenomycin D3 + H2O

Streptomyces glaucescens

the enzyme is involved in the biosynthesis of tetracenomycin C

721576

tetracenomycin F1 + O2

tetracenomycin D3 + H2O

Streptomyces glaucescens

i.e. 3,8,10,12-tetrahydroxy-1-methyl-6,11-dioxo-6,11-dihydrotetracene-2-carboxylate = 6,11-dihydro-3,8,10,12-tetrahydroxy-1-methyl-6,11-dioxo-2-naphthacenecarboxylic acid

721576

i.e. 3,8,10,12-tetrahydroxy-1-methyl-11-oxo-6,11-dihydro-2-tetracenecarboxylate, i.e. 6,11-dihydro-3,8,10,12-tetrahydroxy-1-methyl-11-oxo-2-naphthacenecarboxylic acid

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NATURAL SUBSTRATE

NATURAL PRODUCT

REACTION DIAGRAM

ORGANISM

UNIPROT

COMMENTARY
(Substrate)

LITERATURE
(Substrate)

COMMENTARY
(Product)

LITERATURE
(Product)

REVERSIBILITY
r=reversible
ir=irreversible
?=not specified

tetracenomycin F1 + O2

tetracenomycin D3 + H2O

Streptomyces glaucescens

the enzyme is involved in the biosynthesis of tetracenomycin C

721576

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COFACTOR

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

IMAGE

additional information

Streptomyces glaucescens

does not possess a prosthetic group such as flavin or heme

721576

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METALS and IONS

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

additional information

Streptomyces glaucescens

does not use a metal ion

721576

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INHIBITOR

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

IMAGE

CuCl2

Streptomyces glaucescens

31% loss of activity

721576

diethyl dicarbonate

Streptomyces glaucescens

721576

N-ethylmaleimide

Streptomyces glaucescens

0.025 mM, complete inhibition

721576

p-chloromercuribenzoate

Streptomyces glaucescens

0.025 mM, complete inhibition

721576

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KM VALUE [mM]

SUBSTRATE

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

IMAGE

0.00747

tetracenomycin F1

Streptomyces glaucescens

pH 7.5, 30°C

721576

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SPECIFIC ACTIVITY [µmol/min/mg]

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

0.599

Streptomyces glaucescens

pH 7.5, 30°C

721576

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pH OPTIMUM

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

7.5

Streptomyces glaucescens

721576

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pH RANGE

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

7 - 8

Streptomyces glaucescens

pH 7.0: about 40% of maximal activity, pH 8.0: about 85% of maximal activity

721576

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ORGANISM

COMMENTARY

LITERATURE

UNIPROT

SEQUENCE DB

SOURCE

Streptomyces glaucescens

721576, 722482

brenda

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GENERAL INFORMATION

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

physiological function

Streptomyces glaucescens

the enzyme is involved in the biosynthesis of tetracenomycin C

721576

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UNIPROT

ENTRY NAME

ORGANISM

NO. OF AA

NO. OF TRANSM. HELICES

MOLECULAR WEIGHT[Da]

SOURCE

Sequence

P39889 pBLAST

TCMH_STRGA

Streptomyces glaucescens

112

12683

Swiss-Prot

Show Sequence

A0A3P6WXW2 pBLAST

A0A3P6WXW2_PSEAI

Pseudomonas aeruginosa

125

14056

TrEMBL

Show Sequence

A0A1Y5RG75 pBLAST

A0A1Y5RG75_9RHOB

Pseudoruegeria aquimaris

106

12343

TrEMBL

Show Sequence

A0A2R8BLR6 pBLAST

A0A2R8BLR6_9RHOB

Defluviimonas aquaemixtae

105

12120

TrEMBL

Show Sequence

A0A1Y5T356 pBLAST

A0A1Y5T356_9RHOB

Pelagicola litorisediminis

106

12138

TrEMBL

Show Sequence

A0A1V0RKD3 pBLAST

A0A1V0RKD3_9RHOB

Roseovarius mucosus

106

11975

TrEMBL

Show Sequence

A0A238J5G5 pBLAST

A0A238J5G5_9RHOB

Boseongicola aestuarii

105

11811

TrEMBL

Show Sequence

A0A3P4WDN7 pBLAST

A0A3P4WDN7_PSEAI

Pseudomonas aeruginosa

125

13998

TrEMBL

Show Sequence

A0A0L0JDV8 pBLAST

A0A0L0JDV8_9ACTN

Streptomyces acidiscabies

229

26176

TrEMBL

Show Sequence

A0A2R8C6D4 pBLAST

A0A2R8C6D4_9RHOB

Ruegeria mediterranea M15O_3

106

12145

TrEMBL

Show Sequence

A0A1X6Z638 pBLAST

A0A1X6Z638_9RHOB

Ruegeria meonggei

122

13590

TrEMBL

Show Sequence

A0A2P7ZYN7 pBLAST

A0A2P7ZYN7_9ACTN

Streptomyces sp. 111WW2

113

12129

TrEMBL

Show Sequence

A0A2Z5JXF6 pBLAST

A0A2Z5JXF6_9ACTN

Streptomyces sp. Go-475

233

26230

TrEMBL

Show Sequence

A0A238J889 pBLAST

A0A238J889_9RHOB

Tropicibacter phthalicicus

105

11868

TrEMBL

Show Sequence

A0A132BQC7 pBLAST

A0A132BQC7_9RHOB

Tritonibacter horizontis

106

12132

TrEMBL

Show Sequence

A0A0S4HZZ0 pBLAST

A0A0S4HZZ0_9PSED

Pseudomonas sp. URMO17WK12:I11

121

13695

TrEMBL

Show Sequence

A0A1X6ZE17 pBLAST

A0A1X6ZE17_9RHOB

Ruegeria meonggei

108

12271

TrEMBL

Show Sequence

A0A1X6YAA2 pBLAST

A0A1X6YAA2_9RHOB

Roseovarius albus

106

12254

TrEMBL

Show Sequence

A0A2R8AMF1 pBLAST

A0A2R8AMF1_9RHOB

Aliiroseovarius pelagivivens

106

12241

TrEMBL

Show Sequence

A0A1J5RQD5 pBLAST

A0A1J5RQD5_9ZZZZ

mine drainage metagenome

106

12233

TrEMBL

Show Sequence

A0A1X6YRR0 pBLAST

A0A1X6YRR0_9RHOB

Roseovarius gaetbuli

106

12071

TrEMBL

Show Sequence

A0A3N6E235 pBLAST

A0A3N6E235_9ACTN

Streptomyces sp. ADI95-17

117

13222

TrEMBL

Show Sequence

A0A2N7RK02 pBLAST

A0A2N7RK02_9PSED

Pseudomonas sp. AD21

121

13670

TrEMBL

Show Sequence

A0A0N0D8L5 pBLAST

A0A0N0D8L5_9RHOB

Shimia sp. SK013

106

12184

TrEMBL

Show Sequence

A0A178X5L1 pBLAST

A0A178X5L1_9PSEU

Amycolatopsis sp. M39

106

11443

TrEMBL

Show Sequence

A0A120FZ10 pBLAST

A0A120FZ10_PSEFL

Pseudomonas fluorescens

121

13700

TrEMBL

Show Sequence

A0A238K7M2 pBLAST

A0A238K7M2_9RHOB

Maliponia aquimaris

105

11933

TrEMBL

Show Sequence

A0A238JLL3 pBLAST

A0A238JLL3_9RHOB

Confluentimicrobium lipolyticum

106

12052

TrEMBL

Show Sequence

A0A2W1JIF0 pBLAST

A0A2W1JIF0_9CYAN

Acaryochloris sp. RCC1774

233

25841

TrEMBL

Show Sequence

A0A2R8AQ83 pBLAST

A0A2R8AQ83_9RHOB

Primorskyibacter insulae

105

11918

TrEMBL

Show Sequence

A0A395L520 pBLAST

A0A395L520_9RHIZ

Ensifer sp. M14

101

11032

TrEMBL

Show Sequence

A0A2S6X0I7 pBLAST

A0A2S6X0I7_9ACTN

Streptomyces sp. MH60

235

26220

TrEMBL

Show Sequence

A0A222E2B3 pBLAST

A0A222E2B3_9RHOB

Antarctobacter heliothermus

105

11942

TrEMBL

Show Sequence

A0A109LDT4 pBLAST

A0A109LDT4_PSEFL

Pseudomonas fluorescens

121

13765

TrEMBL

Show Sequence

A0A0N9YTI6 pBLAST

A0A0N9YTI6_9ARCH

Candidatus Nitrosocosmicus oleophilus

103

12001

TrEMBL

Show Sequence

A0A2P7ZJ50 pBLAST

A0A2P7ZJ50_9ACTN

Streptomyces sp. 111WW2

235

26389

TrEMBL

Show Sequence

Entries 1 - 20 of 36

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MOLECULAR WEIGHT

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

12500

Streptomyces glaucescens

3 * 12500, SDS-PAGE

721576

37500

Streptomyces glaucescens

gel filtration

721576

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SUBUNIT

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

trimer

Streptomyces glaucescens

3 * 12500, SDS-PAGE

721576

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PURIFICATION/commentary

ORGANISM

UNIPROT

LITERATURE

Streptomyces glaucescens

721576

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REF.

AUTHORS

TITLE

JOURNAL

VOL.

PAGES

YEAR

ORGANISM (UNIPROT)

PUBMED ID

SOURCE

721576

Shen, B.; Hutchinson, C.R.

Tetracenomycin F1 monooxygenase: oxidation of a naphthacenone to a naphthacenequinone in the biosynthesis of tetracenomycin C in Streptomyces glaucescens

Biochemistry

6656-6663

1993

Streptomyces glaucescens

8329392

brenda

722482

Summers, R.G.; Wendt-Pienkowski, E.; Motamedi, H.; Hutchinson, C.R.

The tcmVI region of the tetracenomycin C biosynthetic gene cluster of Streptomyces glaucescens encodes the tetracenomycin F1 monooxygenase, tetracenomycin F2 cyclase, and, most likely, a second cyclase

J. Bacteriol.

175

7571-7580

1993

Streptomyces glaucescens

8244926

brenda

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