2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate synthase (P17109)

Identification
Name:2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate synthase
Synonyms:
  • SEPHCHC synthase
  • Menaquinone biosynthesis protein menD
Gene Name:menD
Enzyme Class:
Biological Properties
General Function:Involved in thiamine pyrophosphate binding
Specific Function:Catalyzes the thiamine diphosphate-dependent decarboxylation of 2-oxoglutarate and the subsequent addition of the resulting succinic semialdehyde-thiamine pyrophosphate anion to isochorismate to yield 2-succinyl-5-enolpyruvyl-6-hydroxy-3- cyclohexene-1-carboxylate (SEPHCHC)
Cellular Location:Not Available
SMPDB Pathways:
KEGG Pathways:
  • Metabolic pathways eco01100
  • Ubiquinone and other terpenoid-quinone biosynthesis ec00130
KEGG Reactions:
1.0Thumb+1.0Thumb+1.0Thumb ↔ 1.0Thumb+1.0Thumb
1.0alpha-Ketoglutarate + 1.0Hydrogen ion + 1.0Isochorismate ↔ 1.02-Succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate + 1.0Carbon dioxide
ReactionCard
1.0Thumb+1.0Thumb ↔ 1.0Thumb+1.0Thumb
1.0Isochorismate + 1.0alpha-Ketoglutarate ↔ 1.02-Succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate + 1.0Carbon dioxide
ReactionCard
SMPDB Reactions:
1.0isochorismate+1.0Thumb+1.0Thumb+1.0Thumb → 1.0Thumb+1.0Thumb
1.0isochorismate + 1.0Oxoglutaric acid + 1.0Hydrogen ion + 1.0Isochorismate → 1.0Carbon dioxide + 1.02-Succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate
ReactionCard
EcoCyc Reactions:
1.0Thumb+1.0Thumb+1.0Thumb → 1.0Thumb+1.0Thumb
1.0Hydrogen ion + 1.0Isochorismate + 1.0Oxoglutaric acid → 1.02-Succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate + 1.0Carbon dioxide
ReactionCard
Complex Reactions:
1.0Thumb+1.0Thumb → 1.0Thumb+1.0Thumb
1.0Isochorismate + 1.0Oxoglutaric acid → 1.02-Succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate + 1.0Carbon dioxide
ReactionCard
Metabolites:
ECMDB IDNameView
ECMDB200502-Succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylateMetaboCard
ECMDB02812alpha-KetoglutarateMetaboCard
ECMDB04030Carbon dioxideMetaboCard
ECMDB21225Hydrogen ionMetaboCard
ECMDB20162IsochorismateMetaboCard
ECMDB04123Oxoglutaric acidMetaboCard
ECMDB21572Succinate-semialdehyde-thiamine PPiMetaboCard
GO Classification:
Function
2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylic-acid synthase activity
binding
catalytic activity
thiamin pyrophosphate binding
transferase activity
transferase activity, transferring aldehyde or ketonic groups
vitamin binding
Process
fat-soluble vitamin metabolic process
menaquinone biosynthetic process
menaquinone metabolic process
metabolic process
small molecule metabolic process
vitamin K metabolic process
vitamin metabolic process
Gene Properties
Blattner:b2264
Gene OrientationCounterclockwise
Centisome Percentage:51.20
Left Sequence End2375611
Right Sequence End2377281
Gene Sequence:
>1671 bp
ATGTCAGTAAGCGCATTTAACCGACGCTGGGCGGCGGTCATTCTGGAAGCATTAACGCGT
CACGGCGTCAGACACATCTGTATCGCCCCAGGCTCGCGTTCTACACCGTTAACGTTAGCG
GCGGCGGAGAATTCCGCATTCATTCACCACACCCATTTCGATGAGCGTGGGTTGGGGCAT
CTGGCGCTGGGGCTGGCGAAAGTCAGCAAGCAGCCGGTGGCGGTGATTGTGACCTCCGGC
ACGGCGGTGGCAAATCTCTATCCGGCACTGATTGAAGCCGGGTTAACCGGAGAAAAACTG
ATTCTCTTAACCGCCGATCGCCCGCCGGAGCTAATTGACTGCGGCGCGAATCAGGCAATT
CGCCAGCCGGGAATGTTCGCCTCTCACCCCACGCACAGTATTTCATTGCCGCGCCCGACC
CAGGATATCCCCGCACGTTGGCTGGTTTCTACCATCGACCACGCTCTCGGTACGCTTCAT
GCGGGGGGAGTCCATATCAACTGCCCGTTTGCTGAACCGCTGTATGGCGAAATGGACGAT
ACCGGGCTTAGCTGGCAACAGCGTCTGGGTGACTGGTGGCAGGACGACAAACCGTGGCTG
CGTGAAGCGCCTCGTCTGGAAAGTGAAAAACAGCGCGACTGGTTCTTCTGGCGACAAAAG
CGCGGCGTGGTGGTTGCCGGGCGCATGAGTGCGGAAGAGGGCAAAAAAGTTGCCCTGTGG
GCGCAAACTCTTGGCTGGCCGCTGATTGGCGATGTGCTGTCACAAACCGGGCAGCCGCTG
CCGTGTGCCGATCTTTGGTTAGGCAATGCCAAAGCGACCAGCGAGCTGCAGCAGGCGCAA
ATTGTGGTGCAACTGGGAAGCAGCCTGACGGGGAAACGGCTCCTGCAATGGCAGGCAAGC
TGTGAACCAGAAGAGTACTGGATTGTTGATGACATTGAAGGGCGACTTGATCCGGCACAC
CATCGCGGACGTCGCTTAATTGCCAATATTGCCGACTGGCTGGAGCTGCATCCGGCAGAA
AAACGCCAGCCCTGGTGCGTTGAAATCCCGCGCCTGGCGGAACAGGCAATGCAGGCGGTT
ATTGCCCGCCGTGATGCGTTTGGCGAAGCGCAACTGGCGCATCGCATCTGCGACTATCTG
CCTGAACAGGGGCAATTGTTTGTTGGTAACAGCCTGGTGGTACGTCTGATTGATGCGCTT
TCGCAACTTCCGGCAGGTTACCCGGTGTACAGCAACCGTGGGGCCAGCGGTATCGACGGG
CTGCTTTCGACCGCCGCCGGCGTTCAGCGGGCAAGCGGCAAACCGACGCTGGCGATTGTG
GGCGATCTCTCCGCACTTTACGATCTCAACGCGCTGGCGTTATTGCGTCAGGTTTCTGCG
CCGCTGGTATTAATTGTGGTGAACAACAACGGCGGGCAAATTTTCTCGCTGTTGCCAACG
CCGCAAAGCGAGCGTGAGCGTTTCTATCTGATGCCGCAAAACGTCCATTTTGAGCACGCC
GCCGCGATGTTCGAGCTGAAATATCATCGTCCGCAAAACTGGCAGGAACTTGAAACGGCA
TTTGCCGACGCCTGGCGCACGCCAACCACCACGGTGATTGAAATGGTGGTTAACGACACC
GATGGTGCGCAAACGCTCCAGCAACTTCTGGCGCAGGTAAGCCATTTATGA
Protein Properties
Pfam Domain Function:
Protein Residues:556
Protein Molecular Weight:61367
Protein Theoretical pI:7
Signaling Regions:
  • None
Transmembrane Regions:
  • None
Protein Sequence:
>2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate synthase
MSVSAFNRRWAAVILEALTRHGVRHICIAPGSRSTPLTLAAAENSAFIHHTHFDERGLGH
LALGLAKVSKQPVAVIVTSGTAVANLYPALIEAGLTGEKLILLTADRPPELIDCGANQAI
RQPGMFASHPTHSISLPRPTQDIPARWLVSTIDHALGTLHAGGVHINCPFAEPLYGEMDD
TGLSWQQRLGDWWQDDKPWLREAPRLESEKQRDWFFWRQKRGVVVAGRMSAEEGKKVALW
AQTLGWPLIGDVLSQTGQPLPCADLWLGNAKATSELQQAQIVVQLGSSLTGKRLLQWQAS
CEPEEYWIVDDIEGRLDPAHHRGRRLIANIADWLELHPAEKRQPWCVEIPRLAEQAMQAV
IARRDAFGEAQLAHRICDYLPEQGQLFVGNSLVVRLIDALSQLPAGYPVYSNRGASGIDG
LLSTAAGVQRASGKPTLAIVGDLSALYDLNALALLRQVSAPLVLIVVNNNGGQIFSLLPT
PQSERERFYLMPQNVHFEHAAAMFELKYHRPQNWQELETAFADAWRTPTTTVIEMVVNDT
DGAQTLQQLLAQVSHL
References
External Links:
ResourceLink
Uniprot ID:P17109
Uniprot Name:MEND_ECOLI
GenBank Gene ID:AP009048
Genebank Protein ID:85675332
Ecogene ID:EG10579
Ecocyc:EG10579
ColiBase:b2264
Kegg Gene:b2264
EchoBASE ID:EB0574
CCDB:MEND_ECOLI
BacMap:16130199
General Reference:
  • Bhasin, M., Billinsky, J. L., Palmer, D. R. (2003). "Steady-state kinetics and molecular evolution of Escherichia coli MenD [(1R,6R)-2-succinyl-6-hydroxy-2,4-cyclohexadiene-1-carboxylate synthase], an anomalous thiamin diphosphate-dependent decarboxylase-carboligase." Biochemistry 42:13496-13504. Pubmed: 14621995
  • 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
  • Daruwala, R., Kwon, O., Meganathan, R., Hudspeth, M. E. (1996). "A new isochorismate synthase specifically involved in menaquinone (vitamin K2) biosynthesis encoded by the menF gene." FEMS Microbiol Lett 140:159-163. Pubmed: 8764478
  • 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
  • Jiang, M., Cao, Y., Guo, Z. F., Chen, M., Chen, X., Guo, Z. (2007). "Menaquinone biosynthesis in Escherichia coli: identification of 2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate as a novel intermediate and re-evaluation of MenD activity." Biochemistry 46:10979-10989. Pubmed: 17760421
  • Palaniappan, C., Sharma, V., Hudspeth, M. E., Meganathan, R. (1992). "Menaquinone (vitamin K2) biosynthesis: evidence that the Escherichia coli menD gene encodes both 2-succinyl-6-hydroxy-2,4-cyclohexadiene-1-carboxylic acid synthase and alpha-ketoglutarate decarboxylase activities." J Bacteriol 174:8111-8118. Pubmed: 1459959
  • Popp, J. L. (1989). "Sequence and overexpression of the menD gene from Escherichia coli." J Bacteriol 171:4349-4354. Pubmed: 2666397
  • Sieminska, E. A., Macova, A., Palmer, D. R., Sanders, D. A. (2005). "Crystallization and preliminary X-ray analysis of (1R,6R)-2-succinyl-6-hydroxy-2,4-cyclohexadiene-1-carboxylate (SHCHC) synthase (MenD) from Escherichia coli." Acta Crystallogr Sect F Struct Biol Cryst Commun 61:489-492. Pubmed: 16511076
  • Yamamoto, Y., Aiba, H., Baba, T., Hayashi, K., Inada, T., Isono, K., Itoh, T., Kimura, S., Kitagawa, M., Makino, K., Miki, T., Mitsuhashi, N., Mizobuchi, K., Mori, H., Nakade, S., Nakamura, Y., Nashimoto, H., Oshima, T., Oyama, S., Saito, N., Sampei, G., Satoh, Y., Sivasundaram, S., Tagami, H., Horiuchi, T., et, a. l. .. (1997). "Construction of a contiguous 874-kb sequence of the Escherichia coli -K12 genome corresponding to 50.0-68.8 min on the linkage map and analysis of its sequence features." DNA Res 4:91-113. Pubmed: 9205837