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discounted EARLY registration ends Dec 31, 2014
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discounted EARLY registration ends Dec 31, 2014
BioCyc websites MAYBE down
12/28 - 12/31
for maintenance.
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
BioCyc websites MAYBE down
12/28 - 12/31
for maintenance.
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discounted EARLY registration ends Dec 31, 2014
BioCyc websites MAYBE down
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MetaCyc Pathway: factor 430 biosynthesis

Enzyme View:

This view shows enzymes only for those organisms listed below, in the list of taxa known to possess the pathway. If an enzyme name is shown in bold, there is experimental evidence for this enzymatic activity.

Synonyms: F430 biosynthesis

Superclasses: Biosynthesis Cofactors, Prosthetic Groups, Electron Carriers Biosynthesis

Some taxa known to possess this pathway include ? : Methanobacteria , Methanobacterium ivanovii , Methanococci , Methanomicrobia , Methanosarcina , Methanospirillum , Methanothermobacter thermautotrophicus , Methanothermus

Expected Taxonomic Range: Methanobacteria , Methanococci , Methanomicrobia

Summary:
coenzyme F430 is a nickel containing tetrapyrrole cofactor, which is present in all methanogenic bacteria. It was initially observed in 1977 by Jean LeGall in extracts of Methanothermobacter thermautotrophicus. The name factor 430 (F430) was coined by Gunsalus & Wolfe who reported the absorbance maximumat 430 nm [Gunsalus78]. The compound belongs to the corphins, a class of compounds that combine structural elements of both corrins and porphyrins [Eschenmoser86].

In 1982 Ellefson et al showed that coenzyme F430 is a cofactor of the enzyme methyl-coenzyme M reductase (see methyl-coenzyme M reductase I and methyl-coenzyme M reductase II) [Ellefson82]. This enzyme catalyzes the final step of methane production in all methanogenic bacteria: the reduction of the methyl group in methyl-CoM to methane.

F430 exists in two distinct intracellular pools: either bound to methyl-CoM reductase or free of protein in the cytosol. Early literature on F430 was confusing due to reports of heterogeneity in F430 samples that depended on the isolation and purification procedures used in different laboratories. Later work showed that F430 exists primarily in two isomeric forms. These forms differ in the relative stereochemical disposition of acid side chains at positions 12 and 13 [Shiemke88].

The biosynthetic route leading to the formation of coenzyme F430 has not been elucidated completely. It has been shown that it is produced from uroporphyrinogen-III ( which in methanogens is synthesized from L-glutamate), through the intermediate precorrin-2 [Diekert80, Diekert80a, Jaenchen81, Thauer94]. A plausible scheme for the biosynthesis of coenzyme F430 from precorrin-2 has been proposed [Pfaltz87] and is illustrated here. However, all of these reactions are considered hypothetical at the moment.

Credits:
Created 16-May-2006 by Caspi R , SRI International


References

Diekert80: Diekert G, Gilles HH, Jaenchen R, Thauer RK (1980). "Incorporation of 8 succinate per mol nickel into factors F430 by Methanobacterium thermoautotrophicum." Arch Microbiol 128(2);256-62. PMID: 7212929

Diekert80a: Diekert G, Jaenchen R, Thauer RK (1980). "Biosynthetic evidence for a nickel tetrapyrrole structure of factor F430 from Methanobacterium thermoautotrophicum." FEBS Lett 119(1);118-20. PMID: 7428919

Ellefson82: Ellefson WL, Whitman WB, Wolfe RS (1982). "Nickel-containing factor F430: chromophore of the methylreductase of Methanobacterium." Proc Natl Acad Sci U S A 79(12);3707-10. PMID: 6954513

Eschenmoser86: Eschenmoser, E. (1986). "Chemistry of corphinoids." Ann. N. Y. Acad. Sci. 471:108-129.

Gunsalus78: Gunsalus, R. P., Wolfe, R. S. (1978). "Chromophoric factors F342 and F430 of Methanobacterium thermoautotrophicum." FEMS Microbiol. Lett. 3:191-193.

Jaenchen81: Jaenchen, R., Diekert, G., Thauer, R. K. (1981). "Incorporation of methionine-derived methyl groups into factor F430 by Methanobacterium thermoautotrophicum." FEBS Letters 130 (1):133-136.

Pfaltz87: Pfaltz A, Kobelt A, Huster R, Thauer RK (1987). "Biosynthesis of coenzyme F430 in methanogenic bacteria. Identification of 15,17(3)-seco-F430-17(3)-acid as an intermediate." Eur J Biochem 170(1-2);459-67. PMID: 3691535

Shiemke88: Shiemke AK, Hamilton CL, Scott RA (1988). "Structural heterogeneity and purification of protein-free F430 from the cytoplasm of Methanobacterium thermoautotrophicum." J Biol Chem 263(12);5611-6. PMID: 3356701

Thauer94: Thauer RK, Bonacker LG (1994). "Biosynthesis of coenzyme F430, a nickel porphinoid involved in methanogenesis." Ciba Found Symp 180;210-22; discussion 222-7. PMID: 7842854

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

Blanche89: Blanche F, Debussche L, Thibaut D, Crouzet J, Cameron B (1989). "Purification and characterization of S-adenosyl-L-methionine: uroporphyrinogen III methyltransferase from Pseudomonas denitrificans." J Bacteriol 171(8);4222-31. PMID: 2546914

Blanche91: Blanche F, Robin C, Couder M, Faucher D, Cauchois L, Cameron B, Crouzet J (1991). "Purification, characterization, and molecular cloning of S-adenosyl-L-methionine: uroporphyrinogen III methyltransferase from Methanobacterium ivanovii." J Bacteriol 173(15);4637-45. PMID: 1856165

Cantoni84: Cantoni L, Dal Fiume D, Ruggieri R (1984). "Decarboxylation of uroporphyrinogen I and III in 2,3,7,8-tetrachlorodibenzo-p-dioxin induced porphyria in mice." Int J Biochem 16(5);561-5. PMID: 6724109

Goldman93: Goldman BS, Roth JR (1993). "Genetic structure and regulation of the cysG gene in Salmonella typhimurium." J Bacteriol 175(5);1457-66. PMID: 8383112

Hansen97: Hansen J, Muldbjerg M, Cherest H, Surdin-Kerjan Y (1997). "Siroheme biosynthesis in Saccharomyces cerevisiae requires the products of both the MET1 and MET8 genes." FEBS Lett 401(1);20-4. PMID: 9003798

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Warren02: Warren MJ, Raux E, Schubert HL, Escalante-Semerena JC (2002). "The biosynthesis of adenosylcobalamin (vitamin B12)." Nat Prod Rep 19(4);390-412. PMID: 12195810

Woodcock96: Woodcock SC, Warren MJ (1996). "Evidence for a covalent intermediate in the S-adenosyl-L-methionine-dependent transmethylation reaction catalysed by sirohaem synthase." Biochem J 313 ( Pt 2);415-21. PMID: 8573073

Wu91: Wu JY, Siegel LM, Kredich NM (1991). "High-level expression of Escherichia coli NADPH-sulfite reductase: requirement for a cloned cysG plasmid to overcome limiting siroheme cofactor." J Bacteriol 173(1);325-33. PMID: 1987123


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 18.5 on Fri Dec 26, 2014, biocyc11.