ECMDB

Identification

Name:

Dehydroglycine synthase

Synonyms:

Tyrosine lyase

Gene Name:

thiH

Enzyme Class:

4.1.99.19

Biological Properties

General Function:

Involved in catalytic activity

Specific Function:

Catalyzes the radical-mediated cleavage of tyrosine to dehydroglycine and p-cresol

Cellular Location:

Not Available

SMPDB Pathways:

Thiazole Biosynthesis I PW002041
tyrosine biosynthesis PW000806

KEGG Pathways:

Metabolic pathways eco01100
Thiamine metabolism ec00730

KEGG Reactions:

1.0

↔

1.0

1.0L-Tyrosine + 1.0S-Adenosylmethionine + 1.0NADPH ↔ 1.02-iminoacetate + 1.0p-Cresol + 1.05'-Deoxyadenosine + 1.0L-Methionine + 1.0NADP + 1.0Hydrogen ion
ReactionCard

SMPDB Reactions:

1.0L-Tyrosine

1.0NADPH

1.0S-adenosyl-L-methionine

1.0

→

1.0

1.0L-Tyrosine + 1.0NADPH + 1.0S-adenosyl-L-methionine + 1.0L-Tyrosine + 1.0NADPH → 1.0Hydrogen ion + 1.0NADP + 1.0L-Methionine + 1.05'-Deoxyadenosine + 1.0p-Cresol + 1.02-iminoacetate
ReactionCard

1.0

1.0a thiocarboxy-[ThiS-Protein]

→

1.0

1.0a ThiS sulfur-carrier protein

2.0

1.01-Deoxy-D-xylulose 5-phosphate + 1.0Dehydroglycine + 1.0a thiocarboxy-[ThiS-Protein] → 1.02-((2R,5Z)-2-Carboxy-4-methylthiazol-5(2H)-ylidene)ethyl phosphate + 1.0a ThiS sulfur-carrier protein + 2.0Water
ReactionCard

1.0

1.0S-adenosyl-L-methionine

1.0

→

1.0

1.04-Methylcatechol

1.0

1.0L-Tyrosine + 1.0S-adenosyl-L-methionine + 1.0NADPH → 1.0Dehydroglycine + 1.04-Methylcatechol + 1.05'-Deoxyadenosine + 1.0L-Methionine + 1.0NADP + 1.0Hydrogen ion
ReactionCard

EcoCyc Reactions:

1.0

1.0a reduced electron acceptor

→

1.0

1.0an oxidized electron acceptor

1.0

1.0L-Tyrosine + 1.0S-Adenosylmethionine + 1.0a reduced electron acceptor → 1.0Dehydroglycine + 1.0p-Cresol + 1.05'-Deoxyadenosine + 1.0L-Methionine + 1.0an oxidized electron acceptor + 1.0Hydrogen ion
ReactionCard

Complex Reactions:

1.0

1.0IscS with bound sulfur

1.0

→

1.0

2.0

1.0IscS sulfur acceptor protein

1.0

1.0Adenosine triphosphate + 1.0Dehydroglycine + 1.01-Deoxy-D-xylulose 5-phosphate + 1.0Hydrogen ion + 1.0IscS with bound sulfur + 1.0NADPH → 1.04-Methyl-5-(2-phosphoethyl)-thiazole + 1.0Adenosine monophosphate + 1.0Carbon dioxide + 2.0Water + 1.0IscS sulfur acceptor protein + 1.0NADP + 1.0Pyrophosphate
ReactionCard

Metabolites:

ECMDB ID	Name	View
ECMDB01213	1-Deoxy-D-xylulose 5-phosphate	MetaboCard
ECMDB23053	2-((2R,5Z)-2-Carboxy-4-methylthiazol-5(2H)-ylidene)ethyl phosphate	MetaboCard
ECMDB23155	2-iminoacetate	MetaboCard
ECMDB21457	4-Hydroxybenzyl alcohol	MetaboCard
ECMDB20094	4-Methyl-5-(2-phosphoethyl)-thiazole	MetaboCard
ECMDB21174	5'-Deoxyadenosine	MetaboCard
ECMDB00045	Adenosine monophosphate	MetaboCard
ECMDB00538	Adenosine triphosphate	MetaboCard
ECMDB04030	Carbon dioxide	MetaboCard
ECMDB21328	Dehydroglycine	MetaboCard
ECMDB21225	Hydrogen ion	MetaboCard
ECMDB00696	L-Methionine	MetaboCard
ECMDB00158	L-Tyrosine	MetaboCard
ECMDB00217	NADP	MetaboCard
ECMDB04111	NADPH	MetaboCard
ECMDB21349	p-Cresol	MetaboCard
ECMDB04142	Pyrophosphate	MetaboCard
ECMDB01185	S-Adenosylmethionine	MetaboCard
ECMDB00494	Water	MetaboCard

GO Classification:

Function
4 iron, 4 sulfur cluster binding
binding
catalytic activity
cation binding
ion binding
iron ion binding
iron-sulfur cluster binding
metal cluster binding
metal ion binding
transition metal ion binding
Process
cellular aromatic compound metabolic process
cellular metabolic process
cofactor metabolic process
metabolic process
thiamin and derivative metabolic process
thiamin biosynthetic process
thiamin metabolic process

Gene Properties

Blattner:

b3990

Gene Orientation

Counterclockwise

Centisome Percentage:

90.28

Left Sequence End

4188758

Right Sequence End

4189891

Gene Sequence:

>1134 bp
ATGTCATCACTGAATATTAAACAGGGAAGTGACGCTCATTTTCCCGATTATCCTCTGGCG
TCGCCCAGTAATAATGAAATTGATTTACTTAATCTAATCTCAGTTTTATGGCGGGCCAAA
AAAACGGTCATGGCGGTCGTTTTTGCGTTTGCCTGCGCAGGCTTGCTGATCTCTTTCATC
CTGCCGCAAAAATGGACCAGCGCGGCGGTTGTCACGCCTCCAGAACCTGTTCAGTGGCAA
GAGTTGGAGAAATCATTCACTAAGCTTCGTGTGCTGGATCTGGATATCAAAATTGATCGT
ACAGAAGCATTTAACCTGTTTATCAAGAAGTTTCAGTCGGTTAGCTTGCTGGAAGAGTAC
CTGCGTTCATCACCTTATGTGATGGACCAATTAAAAGAGGCGAAAATCGACGAACTGGAT
TTGCATCGCGCAATTGTCGCATTGAGCGAAAAAATGAAAGCGGTTGATGACAATGCCAGT
AAGAAAAAAGATGAACCGTCACTGTATACCTCCTGGACGCTAAGTTTTACCGCGCCAACC
AGTGAAGAGGCGCAGACCGTTTTGAGCGGGTATATCGATTATATCTCTACGTTGGTGGTG
AAAGAGTCGCTAGAAAACGTCCGTAATAAACTGGAGATCAAAACCCAGTTTGAAAAAGAA
AAACTGGCTCAGGATCGCATTAAAACGAAAAATCAACTTGATGCAAACATTCAGCGCCTC
AATTATTCACTCGACATTGCCAACGCGGCAGGAATTAAAAAGCCCGTTTACAGTAATGGT
CAGGCCGTTAAAGATGACCCCGATTTTTCTATTTCTCTCGGTGCAGACGGTATTGAACGC
AAACTGGAAATAGAAAAAGCGGTCACTGACGTTGCGGAACTGAACGGTGAATTACGTAAT
CGGCAGTATCTTGTCGAGCAATTAACAAAAGCACATGTCAACGATGTGAATTTTACGCCG
TTTAAATATCAGTTAAGCCCGTCATTGCCAGTGAAAAAAGACGGTCCGGGTAAGGCGATT
ATTGTGATCCTTTCCGCGTTGATCGGCGGGATGGTGGCTTGTGGTGGCGTGCTGTTGCGC
TATGCGATGGCATCCAGAAAACAGGATGCCATGATGGCAGACCACTTAGTTTAA

Protein Properties

Pfam Domain Function:

Radical_SAM (PF04055 )
BATS (PF06968 )

Protein Residues:

377

Protein Molecular Weight:

43320

Protein Theoretical pI:

Signaling Regions:

None

Transmembrane Regions:

None

Protein Sequence:

>Dehydroglycine synthase
MKTFSDRWRQLDWDDIRLRINGKTAADVERALNASQLTRDDMMALLSPAASGYLEQLAQR
AQRLTRQRFGNTVSFYVPLYLSNLCANDCTYCGFSMSNRIKRKTLDEADIARESAAIREM
GFEHLLLVTGEHQAKVGMDYFRRHLPALREQFSSLQMEVQPLAETEYAELKQLGLDGVMV
YQETYHEATYARHHLKGKKQDFFWRLETPDRLGRAGIDKIGLGALIGLSDNWRVDSYMVA
EHLLWLQQHYWQSRYSVSFPRLRPCTGGIEPASIMDERQLVQTICAFRLLAPEIELSLST
RESPWFRDRVIPLAINNVSAFSKTQPGGYADNHPELEQFSPHDDRRPEAVAAALTAQGLQ
PVWKDWDSYLGRASQRL

References

External Links:

Resource	Link
Uniprot ID:	P30140
Uniprot Name:	THIH_ECOLI
GenBank Gene ID:	AP009048
Genebank Protein ID:	85674708
Ecogene ID:	EG11590
Ecocyc:	EG11590
ColiBase:	b3990
Kegg Gene:	b3990
EchoBASE ID:	EB1548
CCDB:	THIH_ECOLI
BacMap:	16131820

General Reference:

Blattner, F. R., Burland, V., Plunkett, G. 3rd, Sofia, H. J., Daniels, D. L. (1993). "Analysis of the Escherichia coli genome. IV. DNA sequence of the region from 89.2 to 92.8 minutes." Nucleic Acids Res 21:5408-5417. Pubmed: 8265357
Blattner, F. R., Plunkett, G. 3rd, Bloch, C. A., Perna, N. T., Burland, V., Riley, M., Collado-Vides, J., Glasner, J. D., Rode, C. K., Mayhew, G. F., Gregor, J., Davis, N. W., Kirkpatrick, H. A., Goeden, M. A., Rose, D. J., Mau, B., Shao, Y. (1997). "The complete genome sequence of Escherichia coli K-12." Science 277:1453-1462. Pubmed: 9278503
Hayashi, K., Morooka, N., Yamamoto, Y., Fujita, K., Isono, K., Choi, S., Ohtsubo, E., Baba, T., Wanner, B. L., Mori, H., Horiuchi, T. (2006). "Highly accurate genome sequences of Escherichia coli K-12 strains MG1655 and W3110." Mol Syst Biol 2:2006.0007. Pubmed: 16738553
Kelleher, N. L., Taylor, S. V., Grannis, D., Kinsland, C., Chiu, H. J., Begley, T. P., McLafferty, F. W. (1998). "Efficient sequence analysis of the six gene products (7-74 kDa) from the Escherichia coli thiamin biosynthetic operon by tandem high-resolution mass spectrometry." Protein Sci 7:1796-1801. Pubmed: 10082377
Kriek, M., Martins, F., Challand, M. R., Croft, A., Roach, P. L. (2007). "Thiamine biosynthesis in Escherichia coli: identification of the intermediate and by-product derived from tyrosine." Angew Chem Int Ed Engl 46:9223-9226. Pubmed: 17969213
Kriek, M., Martins, F., Leonardi, R., Fairhurst, S. A., Lowe, D. J., Roach, P. L. (2007). "Thiazole synthase from Escherichia coli: an investigation of the substrates and purified proteins required for activity in vitro." J Biol Chem 282:17413-17423. Pubmed: 17403671
Leonardi, R., Fairhurst, S. A., Kriek, M., Lowe, D. J., Roach, P. L. (2003). "Thiamine biosynthesis in Escherichia coli: isolation and initial characterisation of the ThiGH complex." FEBS Lett 539:95-99. Pubmed: 12650933
Vander Horn, P. B., Backstrom, A. D., Stewart, V., Begley, T. P. (1993). "Structural genes for thiamine biosynthetic enzymes (thiCEFGH) in Escherichia coli K-12." J Bacteriol 175:982-992. Pubmed: 8432721

Dehydroglycine synthase (P30140)