1.4.9.1: methylamine dehydrogenase (amicyanin)

This is an abbreviated version!
For detailed information about methylamine dehydrogenase (amicyanin), go to the full flat file.

Reaction

Synonyms

amine dehydrogenase, amine: oxidoreductase (acceptor deaminating), dehydrogenase, amine, EC 1.4.98.1, EC 1.4.99.3, Heme 2, MADH, mauA, methylamine dehydrogenase, primary-amine dehydrogenase, QH-AmDH, QHNDH, quinohaemoprotein amine dehydrogenase, quinohemoprotein amine dehydrogenase, quinohemoprotein amine dehydrogenases, sQH-AmDH

ECTree

     1 Oxidoreductases

         1.4 Acting on the CH-NH₂ group of donors

             1.4.9 With a copper protein as acceptor

                1.4.9.1 methylamine dehydrogenase (amicyanin)

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Results	in table
14	Activating Compound
573	AA Sequence
1	Application
2	CAS Registry Number
12	Cloned(Commentary)
38	Cofactor
16	Crystallization (Commentary)
1	Expression
9	General Information
4	General Stability
35	Inhibitors
88	KM Value [mM]
4	Localization
14	Metals/Ions
38	Molecular Weight [Da]
11	Natural Substrates/ Products (Substrates)
104	Organism
4	Pathway
20	PDB ID
9	pH Optimum
1	pH Range
2	pH Stability
7	Posttranslational Modification
20	Protein Variants
20	Purification (Commentary)
5	Reaction
5	Reaction Type
67	Reference
1	Source Tissue
8	Specific Activity [micromol/min/mg]
1	Storage Stability
104	Substrates and Products (Substrate)
26	Subunits
64	Synonyms
1	Systematic Name
3	Temperature Optimum [°C]
4	Temperature Stability [°C]
64	Turnover Number [1/s]

Substrates Products

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Substrates Products on EC 1.4.9.1 - methylamine dehydrogenase (amicyanin)

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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

1,12-diaminododecane + acceptor + H2O

? + NH3 + reduced acceptor

Pseudomonas sp.

-

-

396572

-

-

?

1,6-diaminohexane + acceptor + H2O

?

Paracoccus denitrificans

-

acceptor: phenazine ethosulfate/2,6-dichlorophenolindophenol

654866, 656086

-

-

?

1,7-diaminoheptane + acceptor + H2O

?

Paracoccus denitrificans

-

acceptor: phenazine ethosulfate/2,6-dichlorophenolindophenol

654866, 656086

-

-

?

1,8-diaminooctane + H2O + acceptor

?

2 entries

1-aminopentane + acceptor + H2O

pentanal + NH3 + reduced acceptor

Paracoccus denitrificans

-

acceptor: phenazine ethosulfate/2,6-dichlorophenolindophenol

654866, 656086

-

-

?

12-aminododecane + acceptor + H2O

dodecanal + NH3 + reduced acceptor

Pseudomonas sp.

-

-

396572

-

-

?

12-aminododecanoic acid + acceptor + H2O

?

Pseudomonas sp.

-

-

396572

-

-

r

2-phenylethylamine + 2 H2O + 2 acceptor

2-phenylacetic acid + NH3 + 2 reduced acceptor

Pseudomonas putida

-

primary amine

686425

-

-

?

2-phenylethylamine + acceptor + H2O

2-phenylacetaldehyde + NH3 + reduced acceptor

Paracoccus denitrificans

-

acceptor: phenazine ethosulfate/2,6-dichlorophenolindophenol

654676

-

-

?

benzylamine + acceptor + H2O

benzaldehyde + NH3 + reduced acceptor

4 entries

benzylamine + H2O + ferricyanide

benzaldehyde + NH3 + reduced ferricyanide

Paracoccus denitrificans

-

-

702763

-

-

?

butylamine + acceptor + H2O

butanal + NH3 + reduced acceptor

4 entries

dithionite + amicyanin + H2O

?

Paracoccus versutus

-

two-electron-reduced MADH is obtained by exposing the enzyme either to a 3fold molar excess of methylamine or to 2 mM dithionite

685296

-

-

?

ethylamine + acceptor + H2O

acetaldehyde + NH3 + reduced acceptor

2 entries

histamine + acceptor + H2O

? + NH3 + reduced acceptor

Paracoccus denitrificans

-

-

396587

-

-

?

methylamine + acceptor + H2O

formaldehyde + NH3 + reduced acceptor

6 entries

methylamine + acceptor + H2O

methanal + NH3 + reduced acceptor

4 entries

methylamine + amicyanin + H2O

formaldehyde + NH3 + reduced amicyanin

Paracoccus denitrificans

-

-

685087, 688702

-

-

?

methylamine + amicyanin + H2O

formaldehyde + reduced amicyanin + NH3

2 entries

methylamine + H2O + 2 amicyanin

formaldehyde + NH3 + 2 reduced amicyanin

3 entries

methylamine + H2O + 2,6-dichloroindophenol

formaldehyde + NH3 + reduced 2,6-dichloroindophenol

Paracoccus denitrificans

-

-

396585

-

-

r

methylamine + H2O + 2,6-dichloroindophenol + phenazine ethosulfate

formaldehyde + NH3 + reduced phenazine ethosulfate + ?

Paracoccus denitrificans

-

-

396585

-

-

r

methylamine + H2O + amicyanin

formaldehyde + ammonia + reduced amicyanin

2 entries

methylamine + H2O + amicyanin

formaldehyde + NH3 + reduced amicyanin

Paracoccus denitrificans

Q51658

-

723880

-

-

?

methylamine + H2O + cytochrome c-550

formaldehyde + NH3 + reduced cytochrome c-550

Paracoccus versutus

-

-

396583

-

-

r

methylamine + H2O + K3Fe(CN)6

formaldehyde + NH3 + reduced K3Fe(CN)6

Paracoccus denitrificans

-

-

396585

-

-

r

n-butylamine + H2O + ferricyanide

butanal + NH3 + reduced ferricyanide

Paracoccus denitrificans

-

-

702763

-

-

?

n-hexylamine + acceptor + H2O

hexanal + NH3 + reduced acceptor

2 entries

n-nonylamine + acceptor + H2O

nonanal + NH3 + reduced acceptor

Pseudomonas sp.

-

-

396572

-

-

?

n-pentylamine + acceptor + H2O

pentanal + NH3 + reduced acceptor

Pseudomonas sp.

-

-

396571

-

-

?

phenylethylamine + acceptor + H2O

phenylacetaldehyde + NH3 + reduced acceptor

3 entries

propylamine + acceptor + H2O

propionaldehyde + NH3 + reduced acceptor

4 entries

RCH2NH2 + acceptor + H2O

RCHO + NH3 + reduced acceptor

13 entries

tryptamine + acceptor + H2O

?

Paracoccus denitrificans

-

-

686104

-

-

?

additional information

?

-

16 entries

1,8-diaminooctane + H2O + acceptor

?

Pseudomonas sp.

-

-

396572

-

-

?

1,8-diaminooctane + H2O + acceptor

?

Pseudomonas sp. K95

-

-

396572

-

-

?

benzylamine + acceptor + H2O

benzaldehyde + NH3 + reduced acceptor

Paracoccus denitrificans

-

-

396585

-

-

?

benzylamine + acceptor + H2O

benzaldehyde + NH3 + reduced acceptor

Paracoccus denitrificans

-

acceptor: phenazine ethosulfate/2,6-dichlorophenolindophenol

654676

-

-

?

benzylamine + acceptor + H2O

benzaldehyde + NH3 + reduced acceptor

Paracoccus denitrificans IFO 12442

-

-

396585

-

-

?

benzylamine + acceptor + H2O

benzaldehyde + NH3 + reduced acceptor

Pseudomonas sp.

-

-

396571

-

-

?

butylamine + acceptor + H2O

butanal + NH3 + reduced acceptor

Paracoccus denitrificans

-

-

396585

-

-

?

butylamine + acceptor + H2O

butanal + NH3 + reduced acceptor

Paracoccus denitrificans

-

acceptor: phenazine ethosulfate/2,6-dichlorophenolindophenol

654676, 654866, 656086

-

-

?

butylamine + acceptor + H2O

butanal + NH3 + reduced acceptor

Paracoccus denitrificans IFO 12442

-

-

396585

-

-

?

butylamine + acceptor + H2O

butanal + NH3 + reduced acceptor

Pseudomonas sp.

-

-

396571

-

-

?

ethylamine + acceptor + H2O

acetaldehyde + NH3 + reduced acceptor

Paracoccus denitrificans

-

-

396585

-

-

?

ethylamine + acceptor + H2O

acetaldehyde + NH3 + reduced acceptor

Paracoccus denitrificans

-

acceptor: phenazine ethosulfate/2,6-dichlorophenolindophenol

654866, 656086

-

-

?

methylamine + acceptor + H2O

formaldehyde + NH3 + reduced acceptor

Hyphomicrobium zavarzinii

-

-

704815

-

-

?

methylamine + acceptor + H2O

formaldehyde + NH3 + reduced acceptor

Hyphomicrobium zavarzinii ZV580

-

-

704815

-

-

?

methylamine + acceptor + H2O

formaldehyde + NH3 + reduced acceptor

Paracoccus denitrificans

-

-

685218, 686104

-

-

?

methylamine + acceptor + H2O

formaldehyde + NH3 + reduced acceptor

Paracoccus denitrificans

-

acceptor: amicyanin

654628

-

-

?

methylamine + acceptor + H2O

formaldehyde + NH3 + reduced acceptor

Paracoccus denitrificans

-

acceptor: phenazine ethosulfate/2,6-dichlorophenolindophenol

654676, 654866, 656086

-

-

?

methylamine + acceptor + H2O

formaldehyde + NH3 + reduced acceptor

Paracoccus versutus

-

-

685296

-

-

?

methylamine + acceptor + H2O

methanal + NH3 + reduced acceptor

Mycobacterium convolutum

-

-

396578

-

-

?

methylamine + acceptor + H2O

methanal + NH3 + reduced acceptor

Paracoccus denitrificans

-

-

396581, 396585

-

-

?

methylamine + acceptor + H2O

methanal + NH3 + reduced acceptor

Paracoccus denitrificans

-

acceptor: phenazine ethosulfate/2,6-dichlorophenolindophenol or amicyanin

656282

-

-

?

methylamine + acceptor + H2O

methanal + NH3 + reduced acceptor

Paracoccus denitrificans IFO 12442

-

-

396585

-

-

?

methylamine + amicyanin + H2O

formaldehyde + reduced amicyanin + NH3

Paracoccus versutus

-

amicyanin is the in vivo electron acceptor

396582

-

-

?

methylamine + amicyanin + H2O

formaldehyde + reduced amicyanin + NH3

Paracoccus versutus

-

two-electron-reduced MADH is obtained by exposing the enzyme either to a 3fold molar excess of methylamine or to 2 mM dithionite. The complex of MADH and amicyanin in solution is studied using nuclear magnetic resonance. Signals of perdeuterated, 15N-enriched amicyanin bound to MADH are observed. Chemical shift perturbation analysis indicates that the dissociation rate constant is 250/sec and that amicyanin assumes a well-defined position in the complex in solution. The most affected residues are in the interface observed in the crystal structure, whereas smaller chemical shift changes extend to deep inside the protein

685296

-

-

?

methylamine + H2O + 2 amicyanin

formaldehyde + NH3 + 2 reduced amicyanin

Paracoccus denitrificans

P22619; P29894

-

741759, 742302, 742338

-

-

?

methylamine + H2O + 2 amicyanin

formaldehyde + NH3 + 2 reduced amicyanin

Paracoccus denitrificans

P22619

-

763938, 765329

-

-

?

methylamine + H2O + 2 amicyanin

formaldehyde + NH3 + 2 reduced amicyanin

Paracoccus denitrificans

-

-

765329

-

-

?

methylamine + H2O + amicyanin

formaldehyde + ammonia + reduced amicyanin

Paracoccus denitrificans

-

electron transfer from MADH to cytochrome c-551i does not involve a ternary complex but occurs via a ping-pong mechanism in which amicyanin uses the same interface for the reactions with MADH and cytochrome c-551i. Amicyanin binds tightly to MADH with an interface that matches the one observed in the crystal structure and that mostly overlaps with the binding site for cytochrome c-551i. Amicyanin can react rapidly with cytochrome c-551i, but association of amicyanin with MADH inhibits this reaction

715266

-

-

?

methylamine + H2O + amicyanin

formaldehyde + ammonia + reduced amicyanin

Paracoccus denitrificans

-

P96A and P96G mutations in amycyanin do not affect the spectroscopic or redox properties of amicyanin but increase the Kd value for complex formation with MADH and alter the kinetic mechanism for the interprotein elcetron transfer reaction. The crystal structure of P96G amicyanin is very similar to that of native amicyanin, but in addition to the change in Pro96, the side chains of residues Phe97 and Arg99, which make contacts with MADH that are important for stabilizing the amicyanin-MADH complex, are oriented differently

714231

-

-

?

n-hexylamine + acceptor + H2O

hexanal + NH3 + reduced acceptor

Pseudomonas sp.

-

-

396572

-

-

?

n-hexylamine + acceptor + H2O

hexanal + NH3 + reduced acceptor

Pseudomonas sp. K95

-

-

396572

-

-

?

phenylethylamine + acceptor + H2O

phenylacetaldehyde + NH3 + reduced acceptor

Paracoccus denitrificans

-

-

396585

-

-

?

phenylethylamine + acceptor + H2O

phenylacetaldehyde + NH3 + reduced acceptor

Paracoccus versutus

-

-

685296

-

-

?

phenylethylamine + acceptor + H2O

phenylacetaldehyde + NH3 + reduced acceptor

Pseudomonas sp.

-

-

396571

-

-

?

propylamine + acceptor + H2O

propionaldehyde + NH3 + reduced acceptor

Paracoccus denitrificans

-

-

396585

-

-

?

propylamine + acceptor + H2O

propionaldehyde + NH3 + reduced acceptor

Paracoccus denitrificans

-

acceptor: phenazine ethosulfate/2,6-dichlorophenolindophenol

654866, 656086

-

-

?

propylamine + acceptor + H2O

propionaldehyde + NH3 + reduced acceptor

Paracoccus denitrificans IFO 12442

-

-

396585

-

-

?

propylamine + acceptor + H2O

propionaldehyde + NH3 + reduced acceptor

Pseudomonas sp.

-

-

396571

-

-

?

RCH2NH2 + acceptor + H2O

RCHO + NH3 + reduced acceptor

Paracoccus denitrificans

-

acceptor 2,6-dichlorophenolindophenol

396581

-

-

?

RCH2NH2 + acceptor + H2O

RCHO + NH3 + reduced acceptor

Paracoccus denitrificans

-

acceptor phenazine ethosulfate or amicyanin

396581

-

-

?

RCH2NH2 + acceptor + H2O

RCHO + NH3 + reduced acceptor

Paracoccus denitrificans

-

acceptor potassium ferricyanide, phenazine ethosulfate, 2,6-dichlorophenolindophenol

396585

-

-

?

RCH2NH2 + acceptor + H2O

RCHO + NH3 + reduced acceptor

Paracoccus denitrificans IFO 12442

-

acceptor potassium ferricyanide, phenazine ethosulfate, 2,6-dichlorophenolindophenol

396585

-

-

?

RCH2NH2 + acceptor + H2O

RCHO + NH3 + reduced acceptor

Paracoccus versutus

-

-

396582

-

-

?

RCH2NH2 + acceptor + H2O

RCHO + NH3 + reduced acceptor

Paracoccus versutus

-

acceptor cytochrome c-550

396583

-

-

?

RCH2NH2 + acceptor + H2O

RCHO + NH3 + reduced acceptor

Pseudomonas putida

-

acceptor phenazine methosulfate

396577

-

-

?

RCH2NH2 + acceptor + H2O

RCHO + NH3 + reduced acceptor

Pseudomonas putida

-

acceptor 2,6-dichlorophenol-indophenol, ferricyanide or cytochrome c

396577

-

-

?

RCH2NH2 + acceptor + H2O

RCHO + NH3 + reduced acceptor

Pseudomonas putida

-

cytochrome c or artificial electron acceptor

396576

-

-

?

RCH2NH2 + acceptor + H2O

RCHO + NH3 + reduced acceptor

Pseudomonas sp.

-

acceptor 2,6-dichlorophenolindophenol

396571

-

-

?

RCH2NH2 + acceptor + H2O

RCHO + NH3 + reduced acceptor

Pseudomonas sp.

-

acceptor phenazine methosulfate

396571, 396572, 396574

-

-

?

RCH2NH2 + acceptor + H2O

RCHO + NH3 + reduced acceptor

Pseudomonas sp.

-

acceptor 3-(4,5-dimethyl-2-thiazolyl)-2,5-diphenyl-2H-tetrazolium bromide and potassium ferricyanide

396571

-

-

?

RCH2NH2 + acceptor + H2O

RCHO + NH3 + reduced acceptor

Pseudomonas sp. K95

-

acceptor phenazine methosulfate

396572

-

-

?

additional information

?

-

Mycobacterium convolutum

-

broad specificity

396578

-

-

?

additional information

?

-

Paracoccus denitrificans

-

amicyanin ami catalyzes the electron transfer from MADH to the terminal oxidase, without the need for any c-type cytochrome. In the absence of either MADH or cytochrome aa3, amicanin is not capable of oxygen reduction on the same time scale. The oxygen consumption depends nearly linearly on the amicyanin concentration up to at least 100 microM. Experiments demonstrate a remarkable number of possibilities for the electron transfer. The interactions appear to be governed exclusively by the electrostatic nature of each of the proteins. Paracoccus denitrificans provides a pool of cytochromes for efficient electron transfer via weak, ill-defined interactions

715290

-

-

?

additional information

?

-

Paracoccus denitrificans

P22619; P29894

methylamine dehydrogenase (MADH) requires the cofactor tryptophan tryptophylquinone (TTQ) for activity

742338

-

-

?

additional information

?

-

Pseudomonas putida

-

broad specificity

396575

-

-

?

additional information

?

-

Pseudomonas putida

-

broad specificity

396576

-

-

?

additional information

?

-

Pseudomonas putida

-

broad specificity

396577

-

-

?

additional information

?

-

Pseudomonas putida

-

not: FMN, NAD+, NADP+

396577

-

-

?

additional information

?

-

Pseudomonas putida

-

little or no activity with isoamines, L-ornithine, L-lysine and certain diamines or polyamines

396576

-

-

?

additional information

?

-

Pseudomonas putida

-

an essential enzyme for the aerobic degradation of many primary amines even though they have quite different chemical structures (aromatic or aliphatic)

686425

-

-

?

additional information

?

-

Pseudomonas putida

-

when different QHNDH mutants (peaA, peaC and peaD) are transformed with a genetic construction containing the peaABCD cluster, all the recombinant strains efficiently catabolized 2-phenylethylamine as well as other primary amines like propyl-, butyl- and pentylamine.

686425

-

-

?

additional information

?

-

Pseudomonas sp.

-

-

396571

-

-

?

additional information

?

-

Pseudomonas sp.

-

broad specificity

396572

-

-

?

additional information

?

-

Pseudomonas sp.

-

broad specificity

396574

-

-

?

additional information

?

-

Pseudomonas sp.

-

nonspecific oxidizing both short and long primary monoamines and diamines, polyamines, L-noradrenaline, histamine, benzylamine and di-n-hexylamine

396572

-

-

?

additional information

?

-

Pseudomonas sp. K95

-

broad specificity

396572

-

-

?

additional information

?

-

Pseudomonas sp. K95

-

nonspecific oxidizing both short and long primary monoamines and diamines, polyamines, L-noradrenaline, histamine, benzylamine and di-n-hexylamine

396572

-

-

?