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Ligand S-methyl-L-methionine

Basic Ligand Information

Molecular Structure

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Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (6 results)

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Show Natural Substrate (6 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.1.1.10

S-methyl-L-methionine + L-homocysteine = 2 L-methionine

692948, 694665, 441387

-

2.1.1.10

S-methyl-L-methionine + L-homocysteine = L-methionine

692820

-

2.1.1.280

S-methyl-L-methionine + L-homocysteine = L-methionine + S-methyl-L-homocysteine

757333

-

2.1.1.280

S-methyl-L-methionine + L-selenocysteine = L-methionine + Se-methyl-L-selenocysteine

724863, 757333, 692948, 692151, 723887, 726194, 723886

-

4.4.1.14

S-methyl-L-methionine + pyridoxal 5'-phosphate = 4-dimethylsulfonium-2-oxobutyrate + pyridoxamine 5'-phosphate

649492

-

4.4.1.14

S-methyl-L-methionine = alpha-ketobutyrate + ammonia + dimethylsulfide

649492

-

2.1.1.10

2 entries

2.1.1.280

2 entries

4.4.1.14

2 entries

In Vivo Product in Enzyme-catalyzed Reactions (1 result)

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Show Natural Product (1 entry)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.1.1.12

S-adenosyl-L-methionine + L-methionine = S-adenosyl-L-homocysteine + S-methyl-L-methionine

0

-

Substrate in Enzyme-catalyzed Reactions (18 results)

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Show Substrate (18 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.1.1.10

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

441387

-

2.1.1.10

S-methyl-L-methionine + L-homocysteine = 2 L-methionine

733302, 441387, 692948, 694665, 756423

-

2.1.1.10

S-methyl-L-methionine + L-homocysteine = ?

441383, 441384, 687808

-

2.1.1.10

S-methyl-L-methionine + L-homocysteine = L-methionine

692820

-

2.1.1.10

S-methyl-L-methionine + selenohomocysteine = ?

692820

-

2.1.1.14

S-methylmethionine + homocysteine = methionine

441322

-

2.1.1.14

S-methylmethionine + L-homocysteine = ?

441322

-

2.1.1.280

S-methyl-L-methionine + DL-selenohomocysteine = ?

692948

-

2.1.1.280

S-methyl-L-methionine + L-homocysteine = L-methionine + S-methyl-L-homocysteine

757333

-

2.1.1.280

S-methyl-L-methionine + L-selenocysteine = L-methionine + Se-methyl-L-selenocysteine

692948, 724863, 757333, 692151, 723887, 726194, 723886

-

2.1.1.5

L-homocysteine + S-methyl-L-methionine = 2 L-methionine

735230

-

2.1.1.5

L-homocysteine + S-methyl-L-methionine = ?

687808

-

2.1.1.5

L-homocysteine + S-methylmethionine = 2 L-methionine

720202

-

2.1.1.5

L-homocysteine + S-methylmethionine = ?

687808

-

2.1.1.10

5 entries

2.1.1.14

2 entries

2.1.1.280

3 entries

2.1.1.5

4 entries

3.13.2.2

S-methylmethionine + H2O = L-homoserine + dimethylsulfide

649259

-

4.1.1.57

S-Methyl-L-Met = 3-Dimethylthiopropanamine + CO2

4721

-

4.4.1.14

S-methyl-L-methionine + pyridoxal 5'-phosphate = 4-dimethylsulfonium-2-oxobutyrate + pyridoxamine 5'-phosphate

649492

-

4.4.1.14

S-methyl-L-methionine = alpha-ketobutyrate + ammonia + dimethylsulfide

649492

-

4.4.1.14

2 entries

Product in Enzyme-catalyzed Reactions (1 result)

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Show Product (1 entry)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.1.1.12

S-adenosyl-L-methionine + L-methionine = S-adenosyl-L-homocysteine + S-methyl-L-methionine

485142, 0

-

Inhibitor in Enzyme-catalyzed Reactions (3 results)

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Show Inhibitors (3 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

2.1.1.12

-

485144

-

2.5.1.4

weak inhibition

639728

-

4.4.1.14

covalent inactivation after elimination of dimethylsulfide

649492

-

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (6 results)

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Show Turnover Number (6 entries)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

2.1.1.5

0.0044

-

wild-type, presence of 150 mM KCl, pH 7.5, 37°C

735230

2.1.1.5

24

-

-

687808

2.1.1.5

38

-

-

687808

4.4.1.14

0.0008

-

transamination

649492

4.4.1.14

0.0016

-

inactivation

649492

4.4.1.14

0.045

-

beta,gamma-elimination

649492

2.1.1.5

3 entries

4.4.1.14

3 entries

K_M Value (11 results)

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Show KM Value (11 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

2.1.1.10

0.029

-

pH 7.5, 30°C

441387

2.1.1.10

0.05

-

pH 7.5, 30°C

441387

2.1.1.10

0.335

-

pH 7.5, 25°C

694665

2.1.1.10

0.94

-

final concentrations of S-methyl-L-methionine ranging from 0.1 mM to 9 mM, lower value than obtained for BHMT (EC 2.1.1.5)

687808

2.1.1.14

0.0022

-

-

441322

2.1.1.14

0.055

-

-

441322

2.1.1.5

0.76

-

-

687808

2.1.1.5

0.94

-

-

687808

2.1.1.5

3

-

-

687808

2.1.1.5

3.4

-

wild-type, presence of 150 mM KCl, pH 7.5, 37°C

735230

2.1.1.10

4 entries

2.1.1.14

2 entries

2.1.1.5

4 entries

4.4.1.14

4.1

-

beta,gamma-elimination

649492

K_i Value (1 result)

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Show KI Value (1 entry)

EC NUMBER

KI VALUE [MM]

KI VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

2.1.1.12

0.226

-

-

485144

References & Links

Literature References (24)

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Show Reference (24 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

4721

-

Purification and properties of L-methionine decarboxylase of Streptomyces sp.

1980

Misono, H.; Kawabata, Y.; Toyosato, M.; Yamamoto, T.; Soda, K.

Bull. Inst. Chem. Res. Kyoto Univ.

58

323-333

441322

-

Sulphur metabolism. F. Enzymes involved in the synthesis of methionine

1990

Madison, J.T.

Methods Plant Biochem.

3

361-369

441383

13572358

Adenosylmethionine-homocysteine transmethylase

1958

Shapiro, S.K.

Biochim. Biophys. Acta

29

405-409

441384

14445542

Assay of S-methylmethionine and S-adenosylmethionine homocysteine transmethylases

1959

Shapiro, S.K.; Yphantis, D.A.

Biochim. Biophys. Acta

36

241-244

441387

10747987

Characterization and functional expression of cDNAs encoding methionine-sensitive and -insensitive homocysteine S-methyltransferases from Arabidopsis

2000

Ranocha, P.; Bourgis, F.; Ziemak, M.J.; Rhodes, D.; Gage, D.A.; Hanson, A.D.

J. Biol. Chem.

275

15962-15968

485142

6078098

S-Adenosyl methionine: methionine methyl transferase from wheat germ

1967

Karr, D.; Tweto, J.; Albersheim, P.

Arch. Biochem. Biophys.

121

732-738

485144

7673218

Purification and properties of S-adenosyl-L-methionine:L-methionine S-methyltransferase from Wollastonia biflora leaves

1995

James, F.; Nolte, K.D.; Hanson, A.D.

J. Biol. Chem.

270

22344-22350

639728

13610898

Enzymatic cleavage of S-adenosylmethionine

1959

Mudd, S.H.

J. Biol. Chem.

234

87-92

649259

-

Accumulation and decomposition of S-methylmethionine in cabbage

2000

Takigawa, S.; Ishii, G.

Acta Hortic.

517

457-462

649492

14678788

S-methylmethionine is both a substrate and an inactivator of 1-aminocyclopropane-1-carboxylate synthase

2004

Ko, S.; Eliot, A.C.; Kirsch, J.F.

Arch. Biochem. Biophys.

421

85-90

687808

18230605

Betaine-homocysteine S-methyltransferase-2 is an S-methylmethionine-homocysteine methyltransferase

2008

Szegedi, S.S.; Castro, C.C.; Koutmos, M.; Garrow, T.A.

J. Biol. Chem.

283

8939-8945

692151

8706715

On the mechanism of selenium tolerance in selenium-accumulating plants. Purification and characterization of a specific selenocysteine methyltransferase from cultured cells of Astragalus bisculatus

1996

Neuhierl, B.; Böck, A.

Eur. J. Biochem.

239

235-238

692820

9882684

S-Methylmethionine metabolism in Escherichia coli

1999

Thanbichler, M.; Neuhierl, B.; Böck A.

J. Bacteriol.

181

662-665

692948

10026151

A family of S-methylmethionine-dependent thiol/selenol methyltransferases. Role in selenium tolerance and evolutionary relation

1999

Neuhierl, B.; Thanbichler, M.; Lottspeich, F.; Böck, A.

J. Biol. Chem.

274

5407-5414

694665

11309147

The S-methylmethionine cycle in angiosperms: ubiquity, antiquity and activity

2001

Ranocha, P.; McNeil, S.D.; Ziemak, M.J.; Li, C.; Tarczynski, M.C.; Hanson, A.D.

Plant J.

25

575-584

720202

22775318

Double-headed sulfur-linked amino acids as first inhibitors for betaine-homocysteine S-methyltransferase 2

2012

Mladkova, J.; Vanek, V.; Budesinsky, M.; Elbert, T.; Demianova, Z.; Garrow, T.A.; Jiracek, J.

J. Med. Chem.

55

6822-6831

723886

-

Cloning and expression of selenocysteine methyltransferase cDNA from Camellia sinensis

2008

Zhu, L.; Jiang, C.; Deng, W.; Gao, X.; Wang, R.; Wan, X.

Acta Physiol. Plant.

30

167-174

723887

-

Selenium tolerance in Astragalus chrysochlorus: Identification of a cDNA fragment encoding a putative Selenocysteine methyltransferase

2010

Ari, S.; Cakir, O.; Turgut-Kara, N.

Acta Physiol. Plant.

32

1085-1092

724863

16515825

Overexpressing both ATP sulfurylase and selenocysteine methyltransferase enhances selenium phytoremediation traits in Indian mustard

2006

LeDuc, D.L.; AbdelSamie, M.; Montes-Bayon, M.; Wu, C.P.; Reisinger, S.J.; Terry, N.

Environ. Pollut.

144

70-76

726194

-

Cloning and molecular characterization of selenocysteine methyltransferase (AchSMT) cDNA from Astragalus chrysochlorus

2013

Cakir, A.; Ari, A.

Plant OMICS

6

100-106

733302

25046177

Plant-driven repurposing of the ancient S-adenosylmethionine repair enzyme homocysteine S-ethyltransferase

2014

Bradbury, L.M.; Ziemak, M.J.; El Badawi-Sidhu, M.; Fiehn, O.; Hanson, A.D.

Biochem. J.

463

279-286

735230

24895213

Specific potassium ion interactions facilitate homocysteine binding to betaine-homocysteine S-methyltransferase

2014

Mladkova, J.; Hladilkova, J.; Diamond, C.E.; Tryon, K.; Yamada, K.; Garrow, T.A.; Jungwirth, P.; Koutmos, M.; Jiracek, J.

Proteins

82

2552-2564

756423

-

Characterization of a selenium-resistance-enhancing homocysteine s-methyltransferase from Aegilops tauschii

2018

Wu, L.; Shang, Y.; Liu, T.; Chen, W.; Liu, B.; Zhang, L.; Liu, D.; Zhang, B.; Zhang, H.

Cereal Res. Commun.

46

263-274

757333

31504785

Identification and functional characterization of a novel selenocysteine methyltransferase from Brassica juncea L.

2019

Chen, M.; Zeng, L.; Luo, X.; Mehboob, M.Z.; Ao, T.; Lang, M.

J. Exp. Bot.

70

6401-6416

Links to other databases for S-methyl-L-methionine

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Show Links (1 entry)

ChEBI

PubChem