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Escherichia coli K-12 substr. MG1655 Pathway: S-methyl-5'-thioadenosine degradation IV
Inferred from experiment

Pathway diagram: S-methyl-5'-thioadenosine degradation IV

If an enzyme name is shown in bold, there is experimental evidence for this enzymatic activity.

Locations of Mapped Genes:

Schematic showing all replicons, marked with selected genes

Synonyms: methylthioadenosine degradation IV

Superclasses: Degradation/Utilization/AssimilationNucleosides and Nucleotides DegradationS-methyl-5'-thioadenosine Degradation

5'-Methylthioadenosine (MTA) is a side product of the spermidine biosynthesis I and aminopropylcadaverine biosynthesis pathways. Many organisms are able to recycle MTA via the S-methyl-5-thio-α-D-ribose 1-phosphate degradation pathway. However, while the E. coli 5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase can hydrolyze MTA to adenine and methylthioribose (MTR), MTR can not be further metabolized and is excreted [Hughes06]. No transporter for MTR is currently known.

Excretion of MTR entails a loss of sulfur, which may explain why putrescine rather than spermidine is the major polyamine in E. coli [Sekowska00].

In early experiments, 5'-methylthioribose was shown to be a normal biosynthetic product that is secreted into the growth medium by E. coli B [Schroeder73].

Review: [Sekowska00, Albers09]

Created 27-May-2009 by Keseler I, SRI International


Albers09: Albers E (2009). "Metabolic characteristics and importance of the universal methionine salvage pathway recycling methionine from 5'-methylthioadenosine." IUBMB Life 61(12);1132-42. PMID: 19946895

Hughes06: Hughes JA (2006). "In vivo hydrolysis of S-adenosyl-L-methionine in Escherichia coli increases export of 5-methylthioribose." Can J Microbiol 52(6);599-602. PMID: 16788729

Schroeder73: Schroeder HR, Barnes CJ, Bohinski RC, Mallette MF (1973). "Biological production of 5-methylthioribose." Can J Microbiol 19(11);1347-54. PMID: 4203512

Sekowska00: Sekowska A, Kung HF, Danchin A (2000). "Sulfur metabolism in Escherichia coli and related bacteria: facts and fiction." J Mol Microbiol Biotechnol 2(2);145-77. PMID: 10939241

Other References Related to Enzymes, Genes, Subpathways, and Substrates of this Pathway

Allart98: Allart B, Gatel M, Guillerm D, Guillerm G (1998). "The catalytic mechanism of adenosylhomocysteine/methylthioadenosine nucleosidase from Escherichia coli--chemical evidence for a transition state with a substantial oxocarbenium character." Eur J Biochem 256(1);155-62. PMID: 9746359

ChoiRhee05: Choi-Rhee E, Cronan JE (2005). "A nucleosidase required for in vivo function of the S-adenosyl-L-methionine radical enzyme, biotin synthase." Chem Biol 12(5);589-93. PMID: 15911379

Clinch12: Clinch K, Evans GB, Frohlich RF, Gulab SA, Gutierrez JA, Mason JM, Schramm VL, Tyler PC, Woolhouse AD (2012). "Transition state analogue inhibitors of human methylthioadenosine phosphorylase and bacterial methylthioadenosine/S-adenosylhomocysteine nucleosidase incorporating acyclic ribooxacarbenium ion mimics." Bioorg Med Chem 20(17);5181-7. PMID: 22854195

Cornell96: Cornell KA, Swarts WE, Barry RD, Riscoe MK (1996). "Characterization of recombinant Eschericha coli 5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase: analysis of enzymatic activity and substrate specificity." Biochem Biophys Res Commun 228(3);724-32. PMID: 8941345

Cornell98: Cornell KA, Riscoe MK (1998). "Cloning and expression of Escherichia coli 5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase: identification of the pfs gene product." Biochim Biophys Acta 1396(1);8-14. PMID: 9524204

Della85: Della Ragione F, Porcelli M, Carteni-Farina M, Zappia V, Pegg AE (1985). "Escherichia coli S-adenosylhomocysteine/5'-methylthioadenosine nucleosidase. Purification, substrate specificity and mechanism of action." Biochem J 232(2);335-41. PMID: 3911944

DiazMejia09: Diaz-Mejia JJ, Babu M, Emili A (2009). "Computational and experimental approaches to chart the Escherichia coli cell-envelope-associated proteome and interactome." FEMS Microbiol Rev 33(1);66-97. PMID: 19054114

Farrar10: Farrar CE, Siu KK, Howell PL, Jarrett JT (2010). "Biotin synthase exhibits burst kinetics and multiple turnovers in the absence of inhibition by products and product-related biomolecules." Biochemistry 49(46);9985-96. PMID: 20961145

Ferro76: Ferro AJ, Barrett A, Shapiro SK (1976). "Kinetic properties and the effect of substrate analogues on 5'-methylthioadenosine nucleosidase from Escherichia coli." Biochim Biophys Acta 438(2);487-94. PMID: 782530

GOA01: GOA, MGI (2001). "Gene Ontology annotation based on Enzyme Commission mapping." Genomics 74;121-128.

GOA01a: GOA, DDB, FB, MGI, ZFIN (2001). "Gene Ontology annotation through association of InterPro records with GO terms."

GOA06: GOA, SIB (2006). "Electronic Gene Ontology annotations created by transferring manual GO annotations between orthologous microbial proteins."

Gutierrez09: Gutierrez JA, Crowder T, Rinaldo-Matthis A, Ho MC, Almo SC, Schramm VL (2009). "Transition state analogs of 5'-methylthioadenosine nucleosidase disrupt quorum sensing." Nat Chem Biol 5(4):251-7. PMID: 19270684

Kim06b: Kim Y, Lew CM, Gralla JD (2006). "Escherichia coli pfs transcription: regulation and proposed roles in autoinducer-2 synthesis and purine excretion." J Bacteriol 188(21);7457-63. PMID: 16950920

Lee01: Lee JE, Cornell KA, Riscoe MK, Howell PL (2001). "Structure of E. coli 5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase reveals similarity to the purine nucleoside phosphorylases." Structure (Camb) 9(10);941-53. PMID: 11591349

Lee03: Lee JE, Cornell KA, Riscoe MK, Howell PL (2003). "Structure of Escherichia coli 5'-methylthioadenosine/ S-adenosylhomocysteine nucleosidase inhibitor complexes provide insight into the conformational changes required for substrate binding and catalysis." J Biol Chem 278(10);8761-70. PMID: 12496243

Lee05b: Lee JE, Singh V, Evans GB, Tyler PC, Furneaux RH, Cornell KA, Riscoe MK, Schramm VL, Howell PL (2005). "Structural rationale for the affinity of pico- and femtomolar transition state analogues of Escherichia coli 5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase." J Biol Chem 280(18);18274-82. PMID: 15746096

Lee05c: Lee JE, Luong W, Huang DJ, Cornell KA, Riscoe MK, Howell PL (2005). "Mutational analysis of a nucleosidase involved in quorum-sensing autoinducer-2 biosynthesis." Biochemistry 44(33);11049-57. PMID: 16101288

Lee05d: Lee JE, Smith GD, Horvatin C, Huang DJ, Cornell KA, Riscoe MK, Howell PL (2005). "Structural snapshots of MTA/AdoHcy nucleosidase along the reaction coordinate provide insights into enzyme and nucleoside flexibility during catalysis." J Mol Biol 352(3);559-74. PMID: 16109423

Longshaw10: Longshaw AI, Adanitsch F, Gutierrez JA, Evans GB, Tyler PC, Schramm VL (2010). "Design and synthesis of potent "sulfur-free" transition state analogue inhibitors of 5'-methylthioadenosine nucleosidase and 5'-methylthioadenosine phosphorylase." J Med Chem 53(18);6730-46. PMID: 20718423

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Please cite the following article in publications resulting from the use of EcoCyc: Nucleic Acids Research 41:D605-12 2013
Page generated by Pathway Tools version 19.5 (software by SRI International) on Sat Apr 30, 2016, biocyc13.