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IUBMB CommentsIn Salmonella typhimurium LT2, under anaerobic conditions, CobU (EC 2.7.7.62 and EC 2.7.1.156), CobT (EC 2.4.2.21), CobC (EC 3.1.3.73) and CobS (EC 2.7.8.26) catalyse reactions in the nucleotide loop assembly pathway, which convert adenosylcobinamide (AdoCbi) into adenosylcobalamin (AdoCbl). CobT and CobC are involved in 5,6-dimethylbenzimidazole activation whereby 5,6-dimethylbenzimidazole is converted to its riboside, alpha-ribazole. The second branch of the nucleotide loop assembly pathway is the cobinamide (Cbi) activation branch where AdoCbi or adenosylcobinamide-phosphate is converted to the activated intermediate AdoCbi-GDP by Cob U. The final step in adenosylcobalamin biosynthesis is the condensation of AdoCbi-GDP with alpha-ribazole, which is catalysed by EC 2.7.8.26, adenosylcobinamide-GDP ribazoletransferase (CobS), to yield adenosylcobalamin. CobU is a bifunctional enzyme that has both kinase (EC 2.7.1.156) and guanylyltransferase (EC 2.7.7.62, adenosylcobinamide-phosphate guanylyltransferase) activities. However, both activities are not required at all times. The kinase activity has been proposed to function only when S. typhimurium is assimilating cobinamide whereas the guanylyltransferase activity is required for both assimilation of exogenous cobinamide and for de novo synthesis of adenosylcobalamin .
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adenosylcobinamide + ATP
adenosylcobinamide phosphate + ADP
-
-
-
-
ir
adenosylcobinamide + GTP
adenosylcobinamide phosphate + GDP
-
-
-
-
ir
adenosylcobinamide phosphate + GTP
adenosylcobinamide-GDP + diphosphate
ATP + 2',5'-dideoxyadenosylcobinamide
2',5'-dideoxyadenosylcobinamide phosphate + ADP
ATP + 5'-deoxyadenosylcobinamide
5'-deoxyadenosylcobinamide phosphate + ADP
ATP + 5'-deoxycytosylcobinamide
5'-deoxycytosylcobinamide phosphate + ADP
ATP + 5'-deoxyguanosylcobinamide
5'-deoxyguanosylcobinamide phosphate + ADP
ATP + 5'-deoxyinosylcobinamide
5'-deoxyinosylcobinamide phosphate + ADP
ATP + adenosylcobinamide
adenosylcobinamide phosphate + ADP
dATP + adenosylcobinamide
adenosylcobinamide phosphate + dADP
-
-
-
?
dGTP + adenosylcobinamide
adenosylcobinamide phosphate + dGDP
-
-
-
?
GTP + adenosylcobinamide
adenosylcobinamide phosphate + GDP
additional information
?
-
adenosylcobinamide phosphate + GTP
adenosylcobinamide-GDP + diphosphate
-
-
-
-
?
adenosylcobinamide phosphate + GTP
adenosylcobinamide-GDP + diphosphate
-
-
-
-
ir
adenosylcobinamide phosphate + GTP
adenosylcobinamide-GDP + diphosphate
-
adenosylcobinamide-phosphate guanylyltransferase activity
-
-
ir
ATP + 2',5'-dideoxyadenosylcobinamide
2',5'-dideoxyadenosylcobinamide phosphate + ADP
-
highest kinase activity
-
?
ATP + 2',5'-dideoxyadenosylcobinamide
2',5'-dideoxyadenosylcobinamide phosphate + ADP
-
highest kinase activity
-
?
ATP + 5'-deoxyadenosylcobinamide
5'-deoxyadenosylcobinamide phosphate + ADP
-
highest kinase activity
-
?
ATP + 5'-deoxyadenosylcobinamide
5'-deoxyadenosylcobinamide phosphate + ADP
-
highest kinase activity
-
?
ATP + 5'-deoxyadenosylcobinamide
5'-deoxyadenosylcobinamide phosphate + ADP
-
-
-
-
?
ATP + 5'-deoxyadenosylcobinamide
5'-deoxyadenosylcobinamide phosphate + ADP
-
highest kinase activity, product generation relative to adenosylcobinamide 102%
-
?
ATP + 5'-deoxycytosylcobinamide
5'-deoxycytosylcobinamide phosphate + ADP
-
substantial amount of activity retains, about 65% of the activity with AdoCbi
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?
ATP + 5'-deoxycytosylcobinamide
5'-deoxycytosylcobinamide phosphate + ADP
-
substantial amount of activity retains, about 65% of the activity with AdoCbi
-
?
ATP + 5'-deoxycytosylcobinamide
5'-deoxycytosylcobinamide phosphate + ADP
-
about 65% of the activity with AdoCbi
-
?
ATP + 5'-deoxyguanosylcobinamide
5'-deoxyguanosylcobinamide phosphate + ADP
-
substantial amount of activity retains, about 65% of the activity with AdoCbi
-
?
ATP + 5'-deoxyguanosylcobinamide
5'-deoxyguanosylcobinamide phosphate + ADP
-
substantial amount of activity retains, about 65% of the activity with AdoCbi
-
?
ATP + 5'-deoxyinosylcobinamide
5'-deoxyinosylcobinamide phosphate + ADP
-
substantial amount of activity retains, about 65% of the activity with AdoCbi
-
?
ATP + 5'-deoxyinosylcobinamide
5'-deoxyinosylcobinamide phosphate + ADP
-
substantial amount of activity retains, about 65% of the activity with AdoCbi
-
?
ATP + 5'-deoxyinosylcobinamide
5'-deoxyinosylcobinamide phosphate + ADP
-
about 55% of the activity with AdoCbi
-
?
ATP + adenosylcobinamide
adenosylcobinamide phosphate + ADP
-
-
-
?
ATP + adenosylcobinamide
adenosylcobinamide phosphate + ADP
-
cobalamin biosynthesis, involved in de novo synthesis of vitamin B12
-
?
ATP + adenosylcobinamide
adenosylcobinamide phosphate + ADP
-
-
-
?
ATP + adenosylcobinamide
adenosylcobinamide phosphate + ADP
-
cobalamin biosynthesis, involved in de novo synthesis of vitamin B12
-
?
ATP + adenosylcobinamide
adenosylcobinamide phosphate + ADP
-
-
-
?
ATP + adenosylcobinamide
adenosylcobinamide phosphate + ADP
-
cobalamin biosynthesis, involved in de novo synthesis of vitamin B12
-
?
ATP + adenosylcobinamide
adenosylcobinamide phosphate + ADP
-
-
-
?
ATP + adenosylcobinamide
adenosylcobinamide phosphate + ADP
-
cobalamin biosynthesis, involved in de novo synthesis of vitamin B12
-
?
ATP + adenosylcobinamide
adenosylcobinamide phosphate + ADP
-
-
-
?
ATP + adenosylcobinamide
adenosylcobinamide phosphate + ADP
-
cobalamin biosynthesis, involved in de novo synthesis of vitamin B12, uses GTP to guanylate itself, then transfers this GMP group to AdoCbi-P to yield AdoCbi-GDP, the final product of the reaction, CobU enzyme in vivo is always guanylated, guanylation is necessary for both kinase and guanyltransferase activity
-
?
ATP + adenosylcobinamide
adenosylcobinamide phosphate + ADP
-
-
-
?
ATP + adenosylcobinamide
adenosylcobinamide phosphate + ADP
-
-
-
?
ATP + adenosylcobinamide
adenosylcobinamide phosphate + ADP
-
-
-
?
ATP + adenosylcobinamide
adenosylcobinamide phosphate + ADP
-
-
-
?
ATP + adenosylcobinamide
adenosylcobinamide phosphate + ADP
-
assembly of the nucleotide loop of cobalamin
-
?
ATP + adenosylcobinamide
adenosylcobinamide phosphate + ADP
-
cobalamin biosynthesis, involved in de novo synthesis of vitamin B12
-
?
ATP + adenosylcobinamide
adenosylcobinamide phosphate + ADP
-
cobalamin biosynthesis, involved in de novo synthesis of vitamin B12
-
?
ATP + adenosylcobinamide
adenosylcobinamide phosphate + ADP
-
late steps of cobalamin biosynthesis, involved in de novo synthesis of vitamin B12, nucleotide loop assembly, enzyme functions only if Salmonella typhimurium is assimilating cobinamide from its environment, CobU becomes less active during the kinase reaction due to the formation of a covalent CobU-AMP complex that holds CobU in an altered conformation
-
?
ATP + adenosylcobinamide
adenosylcobinamide phosphate + ADP
-
adenosylcobinamide kinase activity
-
-
ir
GTP + adenosylcobinamide
adenosylcobinamide phosphate + GDP
-
-
-
?
GTP + adenosylcobinamide
adenosylcobinamide phosphate + GDP
-
-
-
?
GTP + adenosylcobinamide
adenosylcobinamide phosphate + GDP
-
-
-
?
GTP + adenosylcobinamide
adenosylcobinamide phosphate + GDP
-
-
-
?
GTP + adenosylcobinamide
adenosylcobinamide phosphate + GDP
-
-
-
?
GTP + adenosylcobinamide
adenosylcobinamide phosphate + GDP
-
-
-
?
GTP + adenosylcobinamide
adenosylcobinamide phosphate + GDP
-
-
-
?
GTP + adenosylcobinamide
adenosylcobinamide phosphate + GDP
-
-
-
?
GTP + adenosylcobinamide
adenosylcobinamide phosphate + GDP
-
-
-
?
GTP + adenosylcobinamide
adenosylcobinamide phosphate + GDP
-
assembly of the nucleotide loop of cobalamin
-
?
additional information
?
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-
enzyme can bind CTP, UTP, and dCTP, but product formation is not observed, only ATP or GTP generate a catalytically competent conformation of the enzyme, no activity is observed if (CN)2Cbi is used as substrate
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?
additional information
?
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(CN)2Cbi is no substrate, no product formation with CTP, UTP or dCTP
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?
additional information
?
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CobU does not have any detectable ATP:adenosyltransferase activity
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?
additional information
?
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the enzyme is involved in adenosylcobalamin de novo biosynthesis, overview
-
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?
additional information
?
-
-
CobU enzyme is required for synthesis of both coenzyme B12 (alpha ligand: 5,6-dimethylbenzimidazole) and pseudo-coenzyme B12 (alpha ligand: adenine).
-
-
?
additional information
?
-
-
CobU enzyme of the nucleotide loop assembly pathway is a bifunctional enzyme with adenosylcobinamide and adenosylcobinamide-phosphate guanylyltransferase activity, important for de novo synthesis and for cobinamide salvaging
-
-
?
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adenosylcobinamide + ATP
adenosylcobinamide phosphate + ADP
-
-
-
-
ir
adenosylcobinamide + GTP
adenosylcobinamide phosphate + GDP
-
-
-
-
ir
adenosylcobinamide phosphate + GTP
adenosylcobinamide-GDP + diphosphate
ATP + adenosylcobinamide
adenosylcobinamide phosphate + ADP
GTP + adenosylcobinamide
adenosylcobinamide phosphate + GDP
additional information
?
-
adenosylcobinamide phosphate + GTP
adenosylcobinamide-GDP + diphosphate
-
-
-
-
?
adenosylcobinamide phosphate + GTP
adenosylcobinamide-GDP + diphosphate
-
-
-
-
ir
adenosylcobinamide phosphate + GTP
adenosylcobinamide-GDP + diphosphate
-
adenosylcobinamide-phosphate guanylyltransferase activity
-
-
ir
ATP + adenosylcobinamide
adenosylcobinamide phosphate + ADP
-
cobalamin biosynthesis, involved in de novo synthesis of vitamin B12
-
?
ATP + adenosylcobinamide
adenosylcobinamide phosphate + ADP
-
cobalamin biosynthesis, involved in de novo synthesis of vitamin B12
-
?
ATP + adenosylcobinamide
adenosylcobinamide phosphate + ADP
-
cobalamin biosynthesis, involved in de novo synthesis of vitamin B12
-
?
ATP + adenosylcobinamide
adenosylcobinamide phosphate + ADP
-
cobalamin biosynthesis, involved in de novo synthesis of vitamin B12
-
?
ATP + adenosylcobinamide
adenosylcobinamide phosphate + ADP
-
cobalamin biosynthesis, involved in de novo synthesis of vitamin B12, uses GTP to guanylate itself, then transfers this GMP group to AdoCbi-P to yield AdoCbi-GDP, the final product of the reaction, CobU enzyme in vivo is always guanylated, guanylation is necessary for both kinase and guanyltransferase activity
-
?
ATP + adenosylcobinamide
adenosylcobinamide phosphate + ADP
-
-
-
?
ATP + adenosylcobinamide
adenosylcobinamide phosphate + ADP
-
-
-
?
ATP + adenosylcobinamide
adenosylcobinamide phosphate + ADP
-
-
-
?
ATP + adenosylcobinamide
adenosylcobinamide phosphate + ADP
-
assembly of the nucleotide loop of cobalamin
-
?
ATP + adenosylcobinamide
adenosylcobinamide phosphate + ADP
-
cobalamin biosynthesis, involved in de novo synthesis of vitamin B12
-
?
ATP + adenosylcobinamide
adenosylcobinamide phosphate + ADP
-
cobalamin biosynthesis, involved in de novo synthesis of vitamin B12
-
?
ATP + adenosylcobinamide
adenosylcobinamide phosphate + ADP
-
late steps of cobalamin biosynthesis, involved in de novo synthesis of vitamin B12, nucleotide loop assembly, enzyme functions only if Salmonella typhimurium is assimilating cobinamide from its environment, CobU becomes less active during the kinase reaction due to the formation of a covalent CobU-AMP complex that holds CobU in an altered conformation
-
?
ATP + adenosylcobinamide
adenosylcobinamide phosphate + ADP
-
adenosylcobinamide kinase activity
-
-
ir
GTP + adenosylcobinamide
adenosylcobinamide phosphate + GDP
-
-
-
?
GTP + adenosylcobinamide
adenosylcobinamide phosphate + GDP
-
-
-
?
GTP + adenosylcobinamide
adenosylcobinamide phosphate + GDP
-
-
-
?
GTP + adenosylcobinamide
adenosylcobinamide phosphate + GDP
-
-
-
?
GTP + adenosylcobinamide
adenosylcobinamide phosphate + GDP
-
-
-
?
GTP + adenosylcobinamide
adenosylcobinamide phosphate + GDP
-
-
-
?
GTP + adenosylcobinamide
adenosylcobinamide phosphate + GDP
-
-
-
?
GTP + adenosylcobinamide
adenosylcobinamide phosphate + GDP
-
-
-
?
GTP + adenosylcobinamide
adenosylcobinamide phosphate + GDP
-
-
-
?
GTP + adenosylcobinamide
adenosylcobinamide phosphate + GDP
-
assembly of the nucleotide loop of cobalamin
-
?
additional information
?
-
-
the enzyme is involved in adenosylcobalamin de novo biosynthesis, overview
-
-
?
additional information
?
-
-
CobU enzyme is required for synthesis of both coenzyme B12 (alpha ligand: 5,6-dimethylbenzimidazole) and pseudo-coenzyme B12 (alpha ligand: adenine).
-
-
?
additional information
?
-
-
CobU enzyme of the nucleotide loop assembly pathway is a bifunctional enzyme with adenosylcobinamide and adenosylcobinamide-phosphate guanylyltransferase activity, important for de novo synthesis and for cobinamide salvaging
-
-
?
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Warren, M.J.; Raux, E.; Schubert, H.L.; Escalante-Semerena, J.C.
The biosynthesis of adenosylcobalamin (vitamin B12)
Nat. Prod. Rep.
19
390-412
2002
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brenda
O'Toole, G.A.; Escalante-Semerena, J.C.
Purification and characterization of the bifunctional CobU enzyme of Salmonella typhimurium LT2. Evidence for a CobU-GMP intermediate
J. Biol. Chem.
270
23560-23569
1995
Salmonella enterica subsp. enterica serovar Typhimurium
brenda
Thompson, T.B.; Thomas, M.G.; Escalante-Semerena, J.C.; Rayment, I.
Three-dimensional structure of adenosylcobinamide kinase/adenosylcobinamide phosphate guanylyltransferase from Salmonella typhimurium determined to 2.3 resolution
Biochemistry
37
7686-7695
1998
Salmonella enterica subsp. enterica serovar Typhimurium
brenda
Thompson, T.B.; Thomas, M.G.; Escalante-Semerena, J.C.; Rayment, I.
Three-dimensional structure of adenosylcobinamide kinase/adenosylcobinamide phosphate guanylyltransferase (CobU) complexed with GMP: evidence for a substrate-induced transferase active site
Biochemistry
38
12995-13005
1999
Salmonella enterica subsp. enterica serovar Typhimurium
brenda
Thomas, M.G.; Thompson, T.B.; Rayment, I.; Escalante-Semerena, J.C.
Analysis of the adenosylcobinamide kinase/adenosylcobinamide-phosphate guanylyltransferase (CobU) enzyme of Salmonella typhimurium LT2. Identification of residue His-46 as the site of guanylylation
J. Biol. Chem.
275
27576-27586
2000
Salmonella enterica subsp. enterica serovar Typhimurium
brenda
O'Toole, G.A.; Escalante-Semerena, J.C.
cobU-dependent assimilation of nonadenosylated cobinamide in cobA mutants of Salmonella typhimurium
J. Bacteriol.
175
6328-6336
1993
Salmonella enterica subsp. enterica serovar Typhimurium
brenda
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Cloning, sequencing, expression, and single-step purification of the adenosylcobinamide kinase/adenosylcobinamide-phosphate guanylyltransferase (CobU) from Salmonella typhimurium ATCC 19585
Protein Expr. Purif.
42
178-181
2005
Salmonella enterica subsp. enterica serovar Typhimurium
brenda
Otte, M.M.; Woodson, J.D.; Escalante-Semerena, J.C.
The thiamine kinase (YcfN) enzyme plays a minor but significant role in cobinamide salvaging in Salmonella enterica
J. Bacteriol.
189
7310-7315
2007
Salmonella enterica subsp. enterica serovar Typhimurium
brenda
Anderson, P.J.; Lango, J.; Carkeet, C.; Britten, A.; Kraeutler, B.; Hammock, B.D.; Roth, J.R.
One pathway can incorporate either adenine or dimethylbenzimidazole as an alpha-axial ligand of B12 cofactors in Salmonella enterica
J. Bacteriol.
190
1160-1171
2008
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