Information on EC 1.1.1.206 - tropinone reductase I

Substrates: -
Products: -

?

1-propyl-4-piperidone + NADPH + H+

1-propylpiperidin-4-ol + NADP+

Substrates: low activity
Products: -

?

1-propyl-4-piperidone + NADPH + H+

? + NADP+

Substrates: -
Products: -

?

2-pyrrolidone + NADPH + H+

2-hydroxypyrrolidine + NADP+

Substrates: very low activity
Products: -

?

2-pyrrolidone + NADPH + H+

? + NADP+

Substrates: -
Products: -

?

3-methyl-cyclohexanone + NADPH

3-methylcyclohexanol + NADP+

-

Substrates: 85% of the reaction velocity with tropinone
Products: -

?

3-methylcyclohexanone + NADPH

3-methylcyclohexanol + NADP+

4 entries

3-methylcyclohexanone + NADPH + H+

3-methylcyclohexanol + NADP+

3-methylcyclohexanone + NADPH + H+

? + NADP+

Substrates: -
Products: -

?

3-quinuclidinone + NADPH + H+

1-azabicyclo[2.2.2]octan-3-ol + NADP+

4 entries

3-quinuclidinone + NADPH + H+

quinuclidin-3-ol + NADP+

4-chlor-1-methylpiperidine + NADPH + H+

? + NADP+

Substrates: -
Products: -

?

4-chloro-1-methylpiperidine + NADPH + H+

? + NADP+

Substrates: moderate activity
Products: -

?

4-ethylcyclohexanone + NADPH

4-ethylcyclohexanol + NADP+

7 entries

4-ethylcyclohexanone + NADPH + H+

4-ethylcyclohexanol + NADP+

4-methylcyclohexanone + NADPH

4-methylcyclohexanol + NADP+

4-methylcyclohexanone + NADPH + H+

4-methylcyclohexanol + NADP+

6 entries

4-piperidone + NADPH + H+

4-hydroxypiperidin + NADP+

Substrates: very low activity
Products: -

?

4-piperidone + NADPH + H+

? + NADP+

Substrates: -
Products: -

?

4-tetrahydro-thiopyranone + NADPH

?

-

Substrates: 83% of the reaction velocity with tropinone
Products: -

?

7-hydroxytropinone + NADPH

7-hydroxytropan-3-ol + NADP+

8-thiabicyclo(3,2,1)octane-3-one + NADPH

8-thiabicyclo(3,2,1)octane-3-ol + NADP+

-

Substrates: -
Products: -

?

8-thiabicyclo[3.2.1]octan-3-one + NADPH

?

exo-6-hydroxytropinone + NADPH + H+

? + NADP+

N-(2-fluoroethyl)nortropinone + NADPH

N-(2-fluoroethyl)nortropan-3-ol + NADP+

N-isopropylnortropinone + NADPH

N-isopropylnortropan-3-ol + NADP+

N-methyl-4-piperidinone + NADPH

N-methyl-1-piperidinol + NADP+

-

Substrates: 180% of the reaction velocity with tropinone
Products: -

?

N-methyl-4-piperidinone + NADPH + H+

N-methyl-1-piperidinol + NADP+

-

Substrates: 13% of the reaction velocity with tropinone
Products: -

?

N-methyl-4-piperidone + NADPH

1-methylpiperidin-4-ol + NADP+

N-methyl-4-piperidone + NADPH + H+

1-methylpiperidin-4-ol + NADP+

Substrates: low activity
Products: -

?

N-methyl-4-piperidone + NADPH + H+

? + NADP+

Substrates: -
Products: -

?

N-methylpiperidine + NADPH + H+

? + NADP+

N-propyl-4-piperidinone + NADPH

N-propylpiperidinol + NADP+

-

Substrates: 78% of the reaction velocity with tropinone
Products: -

?

N-propyl-4-piperidone + NADPH

1-propylpiperidin-4-ol + NADP+

-

347969

Substrates: -
Products: -

?

nortropine + NADP+

nortropinone + NADPH

quinuclidinone + NADPH

?

scopine + NADP+

scopinone + NADPH

-

Substrates: -
Products: -

?

tetrahydro-4H-thiopyran-4-one + NADPH + H+

? + NADP+

tropine + NADP+

tropinone + NADPH

11 entries

tropine + NADP+

tropinone + NADPH + H+

6 entries

tropinone + NADH + H+

tropine + NAD+

-

Substrates: -
Products: -

r

tropinone + NADPH + H+

pseudotropine + NADP+

tropinone + NADPH + H+

tropine + NADP+

36 entries

additional information

?

-

17 entries

tropine + NADP+

tropinone + NADPH

tropine + NADP+

tropinone + NADPH + H+

A0A6B7HCZ2

760748

Substrates: -
Products: -

r

tropinone + NADPH + H+

pseudotropine + NADP+

tropinone + NADPH + H+

tropine + NADP+

19 entries

additional information

?

-

NADH

-

lower affinity than with NADPH

NADP+

11 entries

NADPH

22 entries

additional information

-

Mg2+

slightly activating

Na+

slightly activating

additional information

8-thiabicyclo(3,2,1)octane-3-one

-

complete inhibition at 4 mM

Ca2+

-

0-15% inactivation at 1 mM

Cd2+

-

26-43% inactivation at 1 mM

Co2+

-

0-15% inactivation at 1 mM

Cu2+

-

99% inactivation at 1 mM

diethyl dicarbonate

-

complete inhibition at 0.1 mM

Fe2+

-

0-15% inactivation at 1 mM

Fe3+

-

0-15% inactivation at 1 mM

Hg2+

-

99% inactivation at 1 mM

K+

slight inhibitory effect at 5 mM

Li+

methyl jasmonate

inhibits expression of TRI in hairy roots

696874

Mg2+

-

0-15% inactivation at 1 mM

Mn2+

-

0-15% inactivation at 1 mM

Na+

slight inhibitory effect at 5 mM

NH4+

slight inhibitory effect at 5 mM

Ni2+

-

0-15% inactivation at 1 mM

p-chloromercuribenzoate

-

strong inhibition at 0.1 and 1.0 mM

p-hydroxymercuribenzoate

-

14% inhibition at 0.01 mM, 56% inhibition at 0.1 mM, 100% inhibition at 1.0 mM

Zn2+

-

0-15% inactivation at 1 mM

additional information

-

not inhibited by EDTA and iodoacetamide

-

additional information

Anisodus acutangulus

B2L2W8

methyl jasmonate can enhance expression of TRI, with weak effect for TRI. TRI is induced weakly in all tissues

696874

-

0.004 - 2.11

3-methylcyclohexanone

0.167 - 5.17

3-quinuclidinone

0.003

4-ethylcyclohexanone

-

0.001 - 8.71

4-methylcyclohexanone

0.003

8-thiabicyclo(3,2,1)octane-3-one

-

0.231

N-Methyl-4-piperidone

-

1.74

N-methylpiperidine

recombinant enzyme, pH 6.7, 30°C

10

NADH

-

0.013 - 0.208

NADP+

8 entries

0.00043 - 0.127

NADPH

7 entries

0.073 - 2

nortropine

3.03

Nortropinone

-

0.91

Scopine

-

0.006 - 114.9

Tropine

9 entries

0.21 - 40.9

tropinone

15 entries

additional information

12 entries

-

8.97

3-methylcyclohexanone

recombinant enzyme, pH 6.7, 30°C

0.54

3-quinuclidinone

pH 9.6, 22°C, recombinant His-tagged enzyme

4.67

4-methylcyclohexanone

pH 6.4, 22°C, recombinant His-tagged enzyme

9.23

N-methylpiperidine

recombinant enzyme, pH 6.7, 30°C

0.54 - 2.94

NADP+

6.76 - 33.34

NADPH

1.67 - 5.69

Tropine

0.98 - 42.26

tropinone

9 entries

5.17

3-methylcyclohexanone

recombinant enzyme, pH 6.7, 30°C

0.1045 - 22.18

3-quinuclidinone

0.0032 - 10.15

4-methylcyclohexanone

4.38

N-methylpiperidine

recombinant enzyme, pH 6.7, 30°C

0.559 - 14

NADP+

53 - 77540

NADPH

0.014 - 10.16

Tropine

0.00094 - 43

tropinone

8 entries

0.316

Pseudomonas sp.

-

crude extract

347970

0.6

Hyoscyamus albus

-

tropinone

1.2

10.2

Hyoscyamus pusillus

-

tropinone

10.8

Hyoscyamus muticus

-

tropinone

15

-

tropinone, strain Hn11

3

Physochlaina orientalis

-

tropinone

30

45

-

tropinone

54

Physalis edulis

-

tropinone

63.82

Pseudomonas sp.

-

purified enzyme

347970

66

Physalis philadelphica

-

tropinone

7.5

additional information

6.1

6.4

6.6

6.7

-

6.8

-

tropinone reduction

6.8 - 8

7

7.6

8

9.5

-

tropine oxidation

9.6

9.9

5.8 - 8.4

-

6.1 - 7

narrow pH range

additional information

25

30

60

-

5.79

6.12

sequence calculation

6.45

sequence analysis

-

UniProt

-

-

-

348024, 656413, 670518

-

Brugmansia sp.

candida x aurea hybrid

347973

-

Cochlearia officinalis

-

UniProt

-

UniProt

-

-

Duboisia leichhardtii

-

-

-

-

-

-

Hyoscyamus bohemicus

-

-

Hyoscyamus canariensis

-

-

Hyoscyamus muticus

-

348024, 670518, 726207, 763572

-

Hyoscyamus muticus Cairo

-

-

and strain Hn11

-

-

-

Hyoscyamus senecionis

no activity in Brassica campestris

-

-

no activity in Browallia americana

-

-

no activity in Calystegia sepium

-

-

no activity in Nicotiana tabacum

-

-

no activity in Physalis alkekengi

-

-

Physalis edulis

-

-

Physalis philadelphica

-

-

Physochlaina orientalis

-

-

AT3

-

AT3

-

Scopolia atropoides

-

-

gene trI

-

cv. Desiree

UniProt

-

UniProt

cv. NMITLI-118

UniProt

low enzyme level, all developmental stages

high enzyme level

additional information

8 entries

Highest Expressing Human Cell Lines

Filter by:

Cell Line Links

Gene Links

evolution

7 entries

malfunction

metabolism

9 entries

physiological function

4 entries

additional information

11 entries

115000

-

gel filtration

28000

29000

-

29340

x * 29340, sequence calculation

29460

sequence analysis

29700

-

30000

-

SDS-PAGE

56000

-

gel filtration

58000

Pseudomonas sp.

-

gel filtration

60000

?

dimer

homodimer

tetramer

additional information

12 entries

hanging-drop vapor diffusion at 20°C

-

348028

A160S

-

higher Km for tropinone that wild type enzyme

H112F

-

higher Km for tropinone that wild type enzyme

H112Y

-

higher Km for tropinone that wild type enzyme

V168E

-

lower Km for tropinone that wild type enzyme

additional information

6 - 10.5

-

4

50

50 - 60

purified recombinant enzyme, retains about 75% of maximal catalytic activity at up to 50°C, 4.27% activity remaining on incubation at 60°C

50 - 80

purified recombinant His-tagged enzyme, pH 6.6, 30 min, over 92% activity remaining at up to 50°C, 30% remaining at 60°C, 7% at 70°C, complete inactivation occurs at 80°C

60

70

75

-

immediate thermal denaturation

80

purified recombinant enzyme, 30 min, inactivation

-18°C, 50% glycerol, 3 weeks

-

4°C, 0.46 mg protein/ml, complete inactivation of enzyme activity over night

-

4°C, 2.3 mg protein/ml, 2 days, complete inactivation of enzyme activity

-

4°C, 23 mg protein/ml, 9 days, complete inactivation of enzyme activity

-

4°C, NADPH, NADP+ and glycerol enhance stability

-

-

partial

-

recombinant His-tagged enzyme from Escherichia coli strain BL21 (DE3) by nickel affinity chromatography

recombinant His-tagged enzyme from Escherichia coli strain BL21(DE3) by nickel affinity chromatography

Solanum dulcamara

-

689953

recombinant His-tagged enzyme from Escherichia coli strain Rosetta by nickel affinity chromatography

recombinant His6-tagged enzyme from Escherichia coli strain BL21(DE3) by affinity chromatography and gel filtration

recombinant His6-tagged enzyme from Escherichia coli strain BL21(DE3) by nickel affinity chromatography

recombinant His6-tagged enzyme from Escherichia coli strain BL21(DE3) by nickel affinity chromatography and gel filtration, followed by ultrafiltration

740981

wild-type and recombinant enzymes from Atropa belladonna root cultures by ammonium sulfate fractionation

-

-

cDNAs encoding two enzymes of tropane-alkaloid biosynthesis, tropinone reductase I and hyoscyamine-6beta-hydroxylase are simultaneously introduced into Nicotiana tabacum using particle bombardment and expressed under the control of the CaMV 35S promoter. The expression leads to the formation of unexpected substances, e.g. acetyltropine. Leaves of transgenic plants show in most cases higher nicotine content than leaves of control plants. In addition nicotine related compounds such as anatabine, nornicotine, bipyridine, anabasine, and myosmine are identified in transgenic tobacco lines and are below detection limit in wild-type plants

-

439278

expression in Escherichia coli

gene DnTR1, sequence comparisons and unrooted phylogenetic tree, recombinant expression of His6-tagged enzyme in Escherichia coli strain BL21(DE3), realtime PCR enzyme expression analysis

740981

gene tr, DNA and amino acid sequence determination and analysis, sequence comparison

Cochlearia officinalis

A7DY56

689548

gene TR-I from roots, DNA and amino acid sequence determination and analysis, sequence comparisons and phylogenetic analysis and tree, recombinant functional overexpression of His6-tagged enzyme in Escherichia coli strain BL21(DE3)

gene TR1, enzyme overexpression via leaves transformation with Agrobacterium tumefaciens AGL0, quantitative PCR enzyme expression analysis

Solanum tuberosum

Q9AR59

741221

gene TR1, expression in Atropa belladonna root cultures, derived from transfected leaves using the transformation system via Agrobacterium rhizogenes strain 15834

P50162

656413

gene trI, DNA and amino acid sequence determination and analysis, expression as His-tagged enzyme in Escherichia coli strain BL21(DE3)

Solanum dulcamara

-

689953

gene TRI, DNA and amino acid sequence determination and analysis, sequence comparisons and phylogenetic analysis and tree, functional recombinant overexpression of His-tagged enzyme in Escherichia coli strain Rosetta

gene TRI, isolated from aerial tissue, DNA and amino acid sequence determination and analysis, sequence comparisons and phylogenetic analysis, overexpression of the His-tagged enzyme in Escherichia coli strain BL21 (DE3)

gene TRI, sequence comparisons

740901

gene WcTR-I, from leaves, DNA and amino acid sequence determination and analysis, sequence comparisons, phylogenetic analysis and tree, recombinant expression of His6-tagged enzyme in Escherichia coli strain BL21(DE3)

quantitative real-time PCR enzyme expression analysis

sixteen different peptide segment exchanges with tropinone reductase II

-

347969

TRI, DNA and amino acid sequence determiation and analysis, phylogenetic analysis and tree, quantitative real-time PCR expression level analysis, recombinant epression in Escherichia coli strain Rosetta (DE3)

A0A6B7HCZ2

760748

TRI-transformed hairy root lines. Full-length fragment of TRI cDNA insert constructed into the pBI121 expression cassette in place of GUS gene. The vector pCAMBIA1304+ contains the TRI gene under control of CaMV35S promoter. Disarmed Agrobacterium tumefaciens strain C58C1 harboring both Agrobacterium rhizogenes Ri plasmid pRiA4 and pCAMBIA1304+, containing a single TRI gene, used for plant transformation

Anisodus acutangulus

B2L2W8

696874

wild-type and recombinant enzymes from Atropa belladonna root cultures by ammonium sulfate fractionation

Atropa belladonna

-

656413

salicylic acid and sodium nitroprusside treatments do not affect the enzyme expression

740981

the enzyme expression is upregulated by methyl jasmonate, but not by salicylate and NO

740901

the enzyme-encoding TR-I gene expression is upregulated on exposure to signal molecules, i.e. methyl jasmonate and salicylic acid, and on mechanical injury/wounding