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Ligand methanethiol

Basic Ligand Information

Molecular Structure

Pathway Source

Pathways

BRENDA

methionine metabolism

KEGG

Cysteine and methionine metabolism, Sulfur metabolism

MetaCyc

dimethyl sulfide biosynthesis from methionine, dimethyl sulfide degradation I, ethene biosynthesis III (microbes), L-methionine degradation II, methanogenesis from dimethylsulfide, methanogenesis from methanethiol, methylthiopropanoate degradation I (cleavage), S-methyl-5-thio-alpha-D-ribose 1-phosphate degradation II, S-methyl-5-thio-alpha-D-ribose 1-phosphate degradation III more

Show all BRENDA pathways known for methanethiol

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Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (5 results)

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Show Natural Substrate (5 entries)

EC NUMBER

LITERATURE

REACTION DIAGRAM

PROVEN IN VIVO REACTION

ENZYME 3D STRUCTURE

1.8.3.4

395103, 395104

methanethiol + O2 + H2O = formaldehyde + H2S + H2O2

-

2.1.1.251

717716

methanethiol + a [Co(I) methylated-thiol-specific corrinoid protein] = a [methyl-Co(III) methylated-thiol-specific corrinoid protein] + hydrogen sulfide

-

2.1.1.251

717563, 717763, 717716

methanethiol + coenzyme M = methyl-CoM + hydrogen sulfide

-

2.1.1.251

2 entries

2.1.1.334

741048, 757021, 757759

S-adenosyl-L-methionine + methanethiol = S-adenosyl-L-homocysteine + dimethyl sulfide

-

2.5.1.49

637329, 637822, 637824, 637832, 662606

O-acetyl-L-homoserine + methanethiol = L-methionine + acetate

-

In Vivo Product in Enzyme-catalyzed Reactions (5 results)

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Show Natural Product (5 entries)

EC NUMBER

LITERATURE

REACTION DIAGRAM

PROVEN IN VIVO REACTION

ENZYME 3D STRUCTURE

2.1.1.251

-

dimethylsulfide + coenzyme M = methyl-CoM + methanethiol

-

4.2.1.155

-

3-(methylthio)acryloyl-CoA + 2 H2O = acetaldehyde + methanethiol + CoA + CO2

-

4.4.1.11

, 649139, 652470, 649323, 650615, 650748, 650770, 651771, 649805, 649595

L-methionine + H2O = methanethiol + NH3 + 2-oxobutanoate

3ael, 3D-view

4.4.1.11

650770, 652470, 650748, 649595, 649805, 651771, 650615, 649323, 649139,

L-methionine + H2O = methanethiol + NH3 + 2-oxobutanoate

3aep, 3D-view

4.4.1.11

2 entries

4.4.1.13

-

L-methionine + H2O = methanethiol + NH3 + 2-oxobutanoate

-

Substrate in Enzyme-catalyzed Reactions (22 results)

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Show Substrate (22 entries)

EC NUMBER

LITERATURE

REACTION DIAGRAM

REACTION

ENZYME 3D STRUCTURE

1.14.13.8

710837

methylmercaptan + NADPH + H+ + O2 = ? + NADP+ + H2O

-

1.8.3.4

395102, 395103, 395101, 395104

methanethiol + O2 + H2O = formaldehyde + H2S + H2O2

-

2.1.1.251

717563, 717763, 717716

methanethiol + a [Co(I) methylated-thiol-specific corrinoid protein] = a [methyl-Co(III) methylated-thiol-specific corrinoid protein] + hydrogen sulfide

-

2.1.1.251

717563, 717716, 717763

methanethiol + coenzyme M = methyl-CoM + hydrogen sulfide

-

2.1.1.251

2 entries

2.1.1.334

741048, 757021, 757759

S-adenosyl-L-methionine + methanethiol = S-adenosyl-L-homocysteine + dimethyl sulfide

-

2.1.1.9

441586

methylmercaptan + S-adenosyl-L-methionine = dimethylsulfide + S-adenosyl-L-homocysteine

-

2.5.1.47

652590

O3-acetyl-L-serine + methylmercaptan = S-methyl-L-cysteine + acetate

-

2.5.1.47

637326, 637350, 637353, 637354, 637327, 637347

O-acetyl-L-Ser + methyl mercaptan = S-methylcysteine + acetate

-

2.5.1.48

637439

O-acetyl-L-homoserine + CH3SH = L-methionine + acetate

-

2.5.1.48

637424, 637429, 676404

O-succinyl-L-homoserine + CH3SH = L-methionine + succinate

-

2.5.1.49

662606, 637832, 637824, 759380, 637822, 722931, 637329

O-acetyl-L-homoserine + methanethiol = L-methionine + acetate

-

2.5.1.49

637822, 637824, 637329

O-acetyl-L-homoserine + methanethiol = L-methionine + acetic acid

-

2.5.1.49

637329, 637331

O-acetyl-L-serine + methanethiol = ?

-

2.5.1.49

637830, 637329, 637331, 637825, 637823, 637824, 637822

O-acetyl-L-homoserine + methyl mercaptan = L-methionine + acetic acid

-

2.5.1.49

637329

O-acetyl-L-serine + methyl mercaptan = S-methylcysteine + ?

-

2.5.1.47

2 entries

2.5.1.48

2 entries

2.5.1.49

5 entries

2.6.1.7

636615

L-vinylglycine + methanethiol = methionine

-

3.1.1.1

651608

methanethiol + acetyl-CoA = methanethioacetate + coenzyme A

-

4.4.1.10

34513

L-Cys + methanethiol = ?

-

4.4.1.9

34718, 34716

L-cysteine + methanethiol = S-methyl-L-cysteine + ?

-

4.4.1.9

652590

O-acetyl-L-serine + methylmercaptan = S-methyl-L-cysteine + acetate

-

4.4.1.9

2 entries

4.5.1.2

34748, 34753

3-chloro-D-alanine + methyl-mercaptane = S-methyl-D-cysteine

-

4.5.1.5

648766

3-chloro-L-alanine + methylmercaptan = S-methyl-L-cysteine + Cl-

-

Product in Enzyme-catalyzed Reactions (46 results)

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Show Product (46 entries)

EC NUMBER

LITERATURE

REACTION DIAGRAM

REACTION

ENZYME 3D STRUCTURE

1.14.13.131

-

dimethyl sulfide + O2 + NADH + H+ = methanethiol + formaldehyde + NAD+ + H2O

-

1.14.13.131

-

dimethyl sulfide + O2 + NADH = methanethiol + formaldehyde + NAD+ + H2O

-

1.14.13.131

2 entries

2.1.1.251

-

dimethylsulfide + coenzyme M = methyl-CoM + methanethiol

-

2.1.1.9

-

bisulfide + S-adenosyl-L-methionine = methanethiol + S-adenosyl-L-homocysteine

-

2.1.1.9

441592,

H2S + S-adenosyl-L-methionine = methanethiol + S-adenosyl-L-homocysteine

-

2.1.1.9

-

S-adenosyl-L-methionine + HS- = S-adenosyl-L-homocysteine + CH3SH

-

2.1.1.9

-

SH- + S-adenosyl-L-methionine = CH3SH + S-adenosyl-L-homocysteine

-

2.1.1.9

4 entries

3.1.2.6

-

S-methyl hydroxy(phenyl)ethanethioate + H2O = methanethiol + hydroxy(phenyl)acetic acid

-

3.2.1.23

-

methylthio-beta-D-galactoside + H2O = galactose + methanethiol

-

3.4.21.19

650308

benzyloxycarbonyl-Glu methylthioester + H2O = benzyloxycarbonyl-Glu + methylthiol

-

3.4.21.19

650308

benzyloxycarbonyl-Glu methylthioester + H2O = benzyloxycarbonyl-L-Glu + methylthiol

-

3.4.21.19

2 entries

3.5.1.2

-

gamma-thiomethyl glutamate + H2O = Glu + thiomethanol

-

3.5.3.18

-

S-methyl-L-thiocitrulline + H2O = L-citrulline + methanethiol

-

3.5.3.18

-

S-methyl-L-thiocitrulline + H2O = methanethiol + L-citrulline

-

3.5.3.18

2 entries

3.8.1.8

-

ametryn + H2O = 4-(ethylamino)-2-hydroxy-6-(isopropylamino)-1,3,5-triazine + H-S-CH3

-

4.1.99.1

-

S-methyl-L-Cys + H2O = methanethiol + pyruvate + NH4+

-

4.1.99.1

-

S-methyl-L-Cys + H2O = pyruvate + NH4+ + methanethiol

-

4.1.99.1

-

S-methyl-L-cysteine + H2O = methanethiol + pyruvate + NH3

-

4.1.99.1

-

S-methyl-L-cysteine + H2O = methanethiol + pyruvate + NH4+

-

4.1.99.2

-

S-methyl-L-cysteine + H2O = methanethiol + pyruvate + NH3

-

4.1.99.2

-

S-methyl-L-cysteine + H2O = methanthiol + pyruvate + NH3

-

4.1.99.1

4 entries

4.1.99.2

2 entries

4.2.1.155

-

3-(methylthio)acryloyl-CoA + 2 H2O = acetaldehyde + methanethiol + CoA + CO2

-

4.4.1.1

, 34509

L-Met = methanethiol + ?

-

4.4.1.1

653162

S-methyl-L-cysteine + H2O = NH3 + pyruvate + methyl mercaptan

-

4.4.1.11

653114

1-amino-3-(methylthio)propylphosphinic acid + H2O = 1-oxopropylphosphinic acid + methanethiol + NH3

3ael, 3D-view

4.4.1.11

653114

1-amino-3-(methylthio)propylphosphinic acid + H2O = 1-oxopropylphosphinic acid + methanethiol + NH3

3aep, 3D-view

4.4.1.11

-

L-1-amino-3-methylthiopropylphosphinic acid + H2O = methanethiol + NH3 + propanoylphosphinic acid

3ael, 3D-view

4.4.1.11

-

L-1-amino-3-methylthiopropylphosphinic acid + H2O = methanethiol + NH3 + propanoylphosphinic acid

3aep, 3D-view

4.4.1.11

-

L-methionine + 2-mercaptoethanol = methanethiol + S-(beta-hydroxyethyl)-L-homocysteine

3ael, 3D-view

4.4.1.11

-

L-methionine + 2-mercaptoethanol = methanethiol + S-(beta-hydroxyethyl)-L-homocysteine

3aep, 3D-view

4.4.1.11

650615, 34517, 649139, , 34516, 649323, 652470, 650748, 649595, 653114, 34534, 650770, 649805, 651771, 34520

L-methionine + H2O = methanethiol + NH3 + 2-oxobutanoate

3ael, 3D-view

4.4.1.11

653114, 649323, 34517, 650615, 649139, , 650770, 651771, 34520, 34534, 649595, 650748, 649805, 652470, 34516

L-methionine + H2O = methanethiol + NH3 + 2-oxobutanoate

3aep, 3D-view

4.4.1.11

-

L-methionine = methanethiol + NH3 + 2-oxobutanoate

3ael, 3D-view

4.4.1.11

-

L-methionine = methanethiol + NH3 + 2-oxobutanoate

3aep, 3D-view

4.4.1.11

-

S-methyl-L-cysteine + H2O = methanethiol + NH3 + 2-oxopropanoate

3ael, 3D-view

4.4.1.11

-

S-methyl-L-cysteine + H2O = methanethiol + NH3 + 2-oxopropanoate

3aep, 3D-view

4.4.1.11

, 34520

S-methyl-L-cysteine + H2O = pyruvate + NH3 + CH3SH

3ael, 3D-view

4.4.1.11

, 34520

S-methyl-L-cysteine + H2O = pyruvate + NH3 + CH3SH

3aep, 3D-view

4.4.1.13

-

(S)-methylcysteine + H2O = methanethiol + pyruvate + NH3

-

4.4.1.13

-

L-methionine + H2O = methanethiol + dimethyl disulfide + dimethyl trisulfide + 2-oxobutyrate

-

4.4.1.13

-

L-methionine + H2O = methanethiol + NH3 + 2-oxobutanoate

-

4.4.1.13

-

L-methionine = methanethiol + (2S)-2-aminobutanoic acid

-

4.4.1.13

-

S-methylmercapto-L-cysteine + H2O = NH3 + pyruvate + methanethiol

-

4.4.1.13

, 34681

S-methyl-L-cysteine = methyl mercaptane + pyruvate + NH3

-

4.4.1.1

2 entries

4.4.1.11

14 entries

4.4.1.13

6 entries

4.4.1.15

-

S-methyl-D-cysteine + H2O = methanethiol + pyruvate + NH3

-

4.4.1.4

-

S-methyl-L-cysteine + H2O = methanethiol + NH3 + 2-oxopropanoate

-

Inhibitor in Enzyme-catalyzed Reactions (3 results)

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Show Inhibitors (3 entries)

COMMENTARY

EC NUMBER

LITERATURE

ENZYME 3D STRUCTURE

-

1.8.3.4

395102, 395103

-

above 0.014 mM

1.8.3.4

395101

-

-

2.5.1.49

637830

-

3D Structure of Enzyme-Ligand-Complex (PDB) (49 results)

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Show 3D Structure of Enzyme-Ligand-Complex (PDB) (49 entries)

EC NUMBER

ENZYME 3D STRUCTURE

1.21.3.1

2bjs, 3D-view

2.3.1.41

2gyo, 3D-view

2.3.1.41

2eft, 3D-view

2.3.1.41

2gyo, 3D-view

2.3.1.41

2eft, 3D-view

2.3.1.41

2gyo, 3D-view

2.3.1.41

2eft, 3D-view

2.3.1.41

2gyo, 3D-view

2.3.1.41

2eft, 3D-view

2.3.1.41

2gyo, 3D-view

2.3.1.41

2eft, 3D-view

2.3.1.41

2gyo, 3D-view

2.3.1.41

2eft, 3D-view

3.5.2.6

5tg5, 3D-view

3.5.2.6

5tg7, 3D-view

3.5.2.6

5tg4, 3D-view

3.5.2.6

5tg5, 3D-view

3.5.2.6

5tg7, 3D-view

3.5.2.6

5tg4, 3D-view

3.5.2.6

5tg5, 3D-view

3.5.2.6

5tg4, 3D-view

3.5.2.6

5tg5, 3D-view

3.5.2.6

5tg7, 3D-view

3.5.2.6

5tg5, 3D-view

3.5.2.6

5tg4, 3D-view

3.5.2.6

5tg7, 3D-view

3.5.2.6

5tg5, 3D-view

3.5.2.6

5tg4, 3D-view

3.5.2.6

5tg5, 3D-view

3.5.2.6

5tg7, 3D-view

3.5.2.6

5tg5, 3D-view

3.5.2.6

5tg4, 3D-view

3.5.2.6

5tg5, 3D-view

3.5.2.6

5tg7, 3D-view

3.5.2.6

5tg5, 3D-view

3.5.2.6

5tg4, 3D-view

4.1.1.32

4yw8, 3D-view

4.4.1.11

3ael, 3D-view

4.4.1.11

3aep, 3D-view

4.4.1.11

3ael, 3D-view

4.4.1.11

3aep, 3D-view

4.4.1.11

3ael, 3D-view

4.4.1.11

3aep, 3D-view

4.4.1.11

3ael, 3D-view

4.4.1.11

3aep, 3D-view

4.4.1.11

3ael, 3D-view

4.4.1.11

3aep, 3D-view

4.4.1.11

3ael, 3D-view

4.4.1.11

3aep, 3D-view

49 entries

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (1 result)

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Show Turnover Number (1 entry)

COMMENTARY

EC NUMBER

LITERATURE

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

pH 7.5, 25°C

2.5.1.49

759380

96.65

-

K_M Value (7 results)

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Show KM Value (7 entries)

COMMENTARY

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

LITERATURE

-

1.8.3.4

0.005

0.01

395101

-

1.8.3.4

0.0097

-

395103

-

1.8.3.4

0.0313

-

395102

-

2.1.1.9

0.24

-

441592

-

4 entries

pH 7.3, 30°C, gamma-replacement reaction

2.5.1.48

100

-

637424

-

2.5.1.49

0.8

-

637823, 637824

pH 7.5, 25°C

2.5.1.49

0.4

-

759380

K_i Value (2 results)

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Show KI Value (2 entries)

COMMENTARY

EC NUMBER

KI VALUE [MM]

KI VALUE MAXIMUM [MM]

LITERATURE

-

1.8.3.4

0.008

-

395103

-

1.8.3.4

0.042

-

395101

-

2 entries

References & Links

Literature References (61)

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Show Reference (61 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

34509

16535512

Purification and characterization of cystathionine gamma-lyase from Lactococcus lactis subsp. cremonis SK11: possible role in flavor compound formation during cheese maturation

1997

Bruinenberg, P.G.; de Roo, G.; Limsowtin, G.K.Y.

Appl. Environ. Microbiol.

63

561-566

34513

782560

The pyridoxal-phosphate-dependent enzymes exclusively catalyzing reactions of beta-replacement

1976

Braunstein, A.E.; Goryachenkova, E.V.

Biochimie

58

5-17

34516

-

The C3-N bond cleavage of 2-amino-3-(N-substituted-amino)-propionic acids catalyzed by L-mehtionine gamma-lyase

1988

Takada, H.; Esaki, N.; Tanaka, H.; Soda, K.

Agric. Biol. Chem.

52

2897-2901

34517

-

Chemical modification of cysteine residues of L-methionine gamma-lyase

1988

Nakayama, T.; Esaki, N.; Tanaka, H.; Soda, K.

Agric. Biol. Chem.

52

177-183

34520

831771

Properties of L-methionine gamma-lyase from Pseudomonas ovalis

1977

Tanaka, H.; Esaki, N.; Soda, K.

Biochemistry

16

100-106

34534

9726878

Purification and characterization of L-methionine gamma-lyase from Brevibacterium linens BL2

1998

Dias, B.; Weimer, B.

Appl. Environ. Microbiol.

64

3327-3331

34681

-

S-Alkylcysteinease: Enzymatic cleavage of S-methyl-L-cysteine and its sulfoxide

1963

Nomura, J.; Nishizuta, Y.; Hayaishi, O.

J. Biol. Chem.

238

1441-1446

34716

-

Purification and properties of beta-cyano-L-alanine synthase from Vicia angustifolia

1989

Ikegami, F.; Takayama, K.; Kurihara, T.; Horiuchi, S.; Tajima, C.; Shirai, R.; Murakoshi, I.

Phytochemistry

28

2285-2291

34718

-

Purification and properties of beta-cyano-L-alanine synthase from Spinacia oleracea

1988

Ikegami, F.; Takayama, K.; Tajima, Ch.; Murakoshi, I.

Phytochemistry

27

2011-2016

34748

6838588

Synthesis of D-cysteine-related amino acids by 3-chloro-D-alanine chloride-lyase of Pseudomonas putida CR 1-1

1983

Nagasawa, T.; Hosano, H.; Ohkishi, H.; Tani, Y.; Yamada, H.

Biochem. Biophys. Res. Commun.

111

809-816

34753

6427787

3-Chloro-D-alanine chloride-lyase (deaminating) of Pseudomonas putida CR 1-1

1984

Nagasawa, T.; Ohkishi, H.; Yamada, H.

Prog. Clin. Biol. Res.

144A

365-375

395101

-

Methyl mercaptan oxidase, a key enzyme in the metabolism of methylated sulphur compounds by Hyphomicrobium EG

1987

Suylen, G.M.H.; Large, P.J.; van Dijken, J.P.; Kuenen, J.G.

J. Gen. Microbiol.

133

2989-2997

395102

-

Purification and properties of methyl mercaptan oxidase from Thiobacillus thioparus TK-m

1992

Gould, W.D.; Kanagawa, T.

J. Gen. Microbiol.

138

217-221

395103

-

Mechanism of oxidation of dimethyl disulphide by Thiobacillus thioparus

1988

Smith, N.A.; Kelly, D.P.

J. Gen. Microbiol.

134

3031-3039

395104

-

Isolation and purification of methyl mercaptan oxidase from Rhodococcus rhodochrous for mercaptan detection

2000

Kim, S.J.; Shin, H.J.; Kim, Y.C.; Yang, J.W.

Biotechnol. Bioprocess Eng.

5

465-468

441586

-

Enzymic methylation of foreign sulfhydryl compounds

1961

Bremer, J.; Greenberg, D.M.

Biochim. Biophys. Acta

46

217-224

441592

7437088

Thiol S-methyltransferase: Suggested role in detoxication of intestinal hydrogen sulfide

1980

Weisiger, R.A.; Pinkus, L.M.; Jakoby, W.B.

Biochem. Pharmacol.

29

2885-2887

636615

-

Deamination and gamma-addition reactions of vinylglycine catalyzed by yeast kynurenine aminotransferase, and suicidal inactivation of the enzyme during its processing

1988

Asada, Y.; Tanizawa, K.; Yonaha, K.; Soda, K.

Agric. Biol. Chem.

52

2873-2878

637326

-

Cysteine biosynthesis: serine transacetylase and O-acetylserine sulfhydrylase

1971

Kredich, N.M.; Becker, M.A.

Methods Enzymol.

17 B

459-470

637327

5656078

Enzymatic synthesis of cysteine and S-methylcysteine in plant extracts

1968

Thompson, J.F.; Moore, D.P.

Biochem. Biophys. Res. Commun.

31

281-287

637329

4609980

Evidence for the identity of O-acetylserine sulfhydrylase with O-acetylhomoserine sulfhydrylase in yeast

1974

Yamagata, S.; Takeshima, K.; Naiki, N.

J. Biochem.

75

1221-1229

637331

795806

O-Acetylserine and O-acetylhomoserine sulfhydrylase of yeast. Further purification and characterization as a pyridoxal enzyme

1976

Yamagata, S.; Takeshima, K.

J. Biochem.

80

777-785

637347

6373737

Enzymatic proof for the identity of the S-sulfocysteine synthase and cysteine synthase B of Salmonella typhimurium

1984

Nakamura, T.; Iwahashi, A.; Eguchi, Y.

J. Bacteriol.

158

1122-1127

637350

-

Purification and properties of cysteine synthase from Spinacia oleracea

1985

Murakoshi, I.; Ikegami, F.; Kaneko, M.

Phytochemistry

24

1907-1911

637353

-

Purification and characterization of cysteine synthases from Citrullus vulgaris

1988

Ikegami, F.; Kaneko, M.; Kamiyama, H.; Murakoshi, I.

Phytochemistry

27

697-701

637354

-

Difference between uracilylalanine synthases and cysteine synthases in Pisum sativum

1987

Ikegami, F.; Kaneko, M.; Lambein, F.; Kuo, Y.H.; Murakoshi, I.

Phytochemistry

26

2699-2704

637424

5340123

Enzymatic synthesis of homocysteine or methionine directly from O-succinyl-homoserine

1967

Flavin, M.; Slaughter, C.

Biochim. Biophys. Acta

132

400-405

637429

-

Cystathionine gamma-synthase (Salmonella)

1971

Kaplan, M.; Guggenheim, S.

Methods Enzymol.

17B

425-433

637439

3816790

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Role of tyrosine 114 of L-methionine gamma-lyase from Pseudomonas putida

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Characterization of L-methionine g-lyase from Cladosporium cladosporioides

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