MetaCyc Pathway: adenosylcobalamin salvage from cobinamide I

Enzyme View:

Pathway diagram: adenosylcobalamin salvage from cobinamide I

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: vitamin B12 biosynthesis

Superclasses: Biosynthesis Cofactors, Prosthetic Groups, Electron Carriers Biosynthesis Vitamins Biosynthesis Cobalamin Biosynthesis Adenosylcobalamin Biosynthesis

Some taxa known to possess this pathway include ? : Escherichia coli K-12 substr. MG1655 Inferred from experiment [Lawrence95], Salmonella enterica enterica serovar Typhimurium

Expected Taxonomic Range: Proteobacteria

De novo synthesis of cobamides requires a great deal of genetic information, which is only found in some prokaryotes. Many bacterial species do not have the full genetic information required for de novo biosynthesis of coenzyme B12, but can synthesize cobalamin when supplied with cobinamide, a stable cobamide that is not a true intermediate of the de novo pathway [Ford55, Lawrence96].

In order to process cobinamide to coenzyme B12, it has to be converted into a real intermediate of the pathway. In most bacteria this is done by the attachment of the upper ligand 5'-deoxyadenosine to yield adenosylcobinamide, followed by phosphorylation to yield adenosyl-cobinamide phosphate, an intermediate of the de novo biosynthetic pathway (this pathway).

Archaebacteria as well as many bacterial species utilze a different salvage pathway, where adenosylcobinamide is first converted to adenosylcobyrate (see adenosylcobalamin salvage from cobinamide II).

Variants: adenosylcobalamin biosynthesis I (early cobalt insertion) , adenosylcobalamin biosynthesis II (late cobalt incorporation) , adenosylcobalamin salvage from cobalamin , adenosylcobalamin salvage from cobinamide II

Unification Links: EcoCyc:COBALSYN-PWY

Created 15-Oct-1996 by Riley M , Marine Biological Laboratory


Ford55: Ford JE, Holdsworth ES, Kon SK (1955). "The biosynthesis of vitamin B12-like compounds." Biochem J 59(1);86-93. PMID: 14351147

Lawrence95: Lawrence JG, Roth JR (1995). "The cobalamin (coenzyme B12) biosynthetic genes of Escherichia coli." J Bacteriol 1995;177(22);6371-80. PMID: 7592411

Lawrence96: Lawrence JG, Roth JR (1996). "Evolution of coenzyme B12 synthesis among enteric bacteria: evidence for loss and reacquisition of a multigene complex." Genetics 142(1);11-24. PMID: 8770581

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

Blanche91: Blanche F, Debussche L, Famechon A, Thibaut D, Cameron B, Crouzet J (1991). "A bifunctional protein from Pseudomonas denitrificans carries cobinamide kinase and cobinamide phosphate guanylyltransferase activities." J Bacteriol 1991;173(19);6052-7. PMID: 1655696

Buan06: Buan NR, Rehfeld K, Escalante-Semerena JC (2006). "Studies of the CobA-type ATP:Co(I)rrinoid adenosyltransferase enzyme of Methanosarcina mazei strain Go1." J Bacteriol 188(10);3543-50. PMID: 16672609

Cameron91: Cameron B, Blanche F, Rouyez MC, Bisch D, Famechon A, Couder M, Cauchois L, Thibaut D, Debussche L, Crouzet J (1991). "Genetic analysis, nucleotide sequence, and products of two Pseudomonas denitrificans cob genes encoding nicotinate-nucleotide: dimethylbenzimidazole phosphoribosyltransferase and cobalamin (5'-phosphate) synthase." J Bacteriol 1991;173(19);6066-73. PMID: 1917841

Chen95: Chen P, Ailion M, Weyand N, Roth J (1995). "The end of the cob operon: evidence that the last gene (cobT) catalyzes synthesis of the lower ligand of vitamin B12, dimethylbenzimidazole." J Bacteriol 177(6);1461-9. PMID: 7883701

Cheong01: Cheong CG, Escalante-Semerena JC, Rayment I (2001). "Structural investigation of the biosynthesis of alternative lower ligands for cobamides by nicotinate mononucleotide: 5,6-dimethylbenzimidazole phosphoribosyltransferase from Salmonella enterica." J Biol Chem 276(40);37612-20. PMID: 11441022

Cheong99: Cheong CG, Escalante-Semerena JC, Rayment I (1999). "The three-dimensional structures of nicotinate mononucleotide:5,6- dimethylbenzimidazole phosphoribosyltransferase (CobT) from Salmonella typhimurium complexed with 5,6-dimethybenzimidazole and its reaction products determined to 1.9 A resolution." Biochemistry 38(49);16125-35. PMID: 10587435

Daley05: Daley DO, Rapp M, Granseth E, Melen K, Drew D, von Heijne G (2005). "Global topology analysis of the Escherichia coli inner membrane proteome." Science 308(5726);1321-3. PMID: 15919996

Debussche91: Debussche L, Couder M, Thibaut D, Cameron B, Crouzet J, Blanche F (1991). "Purification and partial characterization of Cob(I)alamin adenosyltransferase from Pseudomonas denitrificans." J Bacteriol 1991;173(19);6300-2. PMID: 1917862

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

EscalanteSemere90: Escalante-Semerena JC, Suh SJ, Roth JR (1990). "cobA function is required for both de novo cobalamin biosynthesis and assimilation of exogenous corrinoids in Salmonella typhimurium." J Bacteriol 172(1);273-80. PMID: 2403541

GOA01: GOA, DDB, FB, MGI, ZFIN (2001). "Gene Ontology annotation through association of InterPro records with GO terms."

GOA01a: GOA, MGI (2001). "Gene Ontology annotation based on Enzyme Commission mapping." Genomics 74;121-128.

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

Hsu05: Hsu FC, Ho TJ, Lai CC, Lin CF, Chen HP (2005). "Cloning, sequencing, expression, and single-step purification of the adenosylcobinamide kinase/adenosylcobinamide-phosphate guanylyltransferase (CobU) from Salmonella typhimurium ATCC 19585." Protein Expr Purif 42(1);178-81. PMID: 15939305

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

MaggioHall04: Maggio-Hall LA, Claas KR, Escalante-Semerena JC (2004). "The last step in coenzyme B(12) synthesis is localized to the cell membrane in bacteria and archaea." Microbiology 150(Pt 5);1385-95. PMID: 15133100

MaggioHall99: Maggio-Hall LA, Escalante-Semerena JC (1999). "In vitro synthesis of the nucleotide loop of cobalamin by Salmonella typhimurium enzymes." Proc Natl Acad Sci U S A 96(21);11798-803. PMID: 10518530

Minot26: Minot, G.R., Murphy, W.P. (1926). "Treatment of pernicious anaemia by a special diet." J. Am. Med. Assoc. 87:470-476.

Neidhardt96: Neidhardt FC, Curtiss III R, Ingraham JL, Lin ECC, Low Jr KB, Magasanik B, Reznikoff WS, Riley M, Schaechter M, Umbarger HE "Escherichia coli and Salmonella, Cellular and Molecular Biology, Second Edition." American Society for Microbiology, Washington, D.C., 1996.

OToole94: O'Toole GA, Trzebiatowski JR, Escalante-Semerena JC (1994). "The cobC gene of Salmonella typhimurium codes for a novel phosphatase involved in the assembly of the nucleotide loop of cobalamin." J Biol Chem 1994;269(42);26503-11. PMID: 7929373

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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
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