Adenosylcobalamin: Difference between revisions

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{{Short description|Biologically active form of vitamin B12}}
{{Short description|Biologically active form of vitamin B12}}
{{Drugbox
{{Drugbox
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'''Adenosylcobalamin''' (AdoCbl), also known as '''coenzyme B<sub>12</sub>''', '''cobamamide''', and '''dibencozide''', is, along with [[methylcobalamin]] (MeCbl), one of the biologically active forms of [[vitamin B12|vitamin B<sub>12</sub>]].
'''Adenosylcobalamin''' (AdoCbl), also known as '''coenzyme B<sub>12</sub>''', '''cobamamide''', and '''dibencozide''', is, along with [[methylcobalamin]] (MeCbl), one of the biologically active forms of [[vitamin B12|vitamin B<sub>12</sub>]].


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Adenosylcobalamin participates as a cofactor in radical-mediated 1,2-carbon skeleton rearrangements. These processes require the formation of the [[deoxyadenosyl radical]] through homolytic dissociation of the carbon-cobalt bond. This bond is exceptionally weak, with a bond dissociation energy of 31 kcal/mol, which is further lowered in the chemical environment of an enzyme [[active site]]. An [[enzyme]] that uses adenosylcobalamin as a [[Cofactor (biochemistry)|cofactor]] is [[methylmalonyl-CoA mutase]] (MCM).
Adenosylcobalamin participates as a cofactor in radical-mediated 1,2-carbon skeleton rearrangements. These processes require the formation of the [[deoxyadenosyl radical]] through homolytic dissociation of the carbon-cobalt bond. This bond is exceptionally weak, with a bond dissociation energy of 31 kcal/mol, which is further lowered in the chemical environment of an enzyme [[active site]]. An [[enzyme]] that uses adenosylcobalamin as a [[Cofactor (biochemistry)|cofactor]] is [[methylmalonyl-CoA mutase]] (MCM).


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Further experimentation has also determined adenosylcobalamin's role in regulating expression of some bacterial genes. By binding to CarH, AdoCbl can modulate [[carotenoid]] genes, which confer warm colors onto various plants. Carotenoid transcription is activated by sunlight, due to the response from AdoCbl. There are other photoreceptors across different bacterial communities, aside from CarH, that also have reactive capability when bound to AdoCbl. For instance, AerR is another factor that uses AdoCbl to give off purple pigmentation. Additional examination of  adenosylcobalamin-bound enzymes and the development of this cofactor over time may prove to hold regulatory function of DNA and RNA.
Further experimentation has also determined adenosylcobalamin's role in regulating expression of some bacterial genes. By binding to CarH, AdoCbl can modulate [[carotenoid]] genes, which confer warm colors onto various plants. Carotenoid transcription is activated by sunlight, due to the response from AdoCbl. There are other photoreceptors across different bacterial communities, aside from CarH, that also have reactive capability when bound to AdoCbl. For instance, AerR is another factor that uses AdoCbl to give off purple pigmentation. Additional examination of  adenosylcobalamin-bound enzymes and the development of this cofactor over time may prove to hold regulatory function of DNA and RNA.


== See also ==
== See also == <!--T:4-->
* [[Methylcobalamin]]
* [[Methylcobalamin]]
* [[Hydroxocobalamin]]
* [[Hydroxocobalamin]]
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* [[Nitric oxide]]
* [[Nitric oxide]]


== External links ==
== External links == <!--T:5-->
* {{ATC|B03|BA04}}
* {{ATC|B03|BA04}}


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{{Enzyme cofactors}}
{{Enzyme cofactors}}
{{Vitamin}}
{{Vitamin}}


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{{二次利用|date=25 March 2024}}
{{二次利用|date=25 March 2024}}
[[Category:B vitamins]]
[[Category:B vitamins]]

Latest revision as of 11:07, 6 April 2024

Adenosylcobalamin
Clinical data
AHFS/Drugs.comInternational Drug Names
Routes of
administration
Oral
ATC code
Legal status
Legal status
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
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Chemical and physical data
FormulaC72H100CoN18O17P
Molar mass1579.608 g·mol−1
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Adenosylcobalamin (AdoCbl), also known as coenzyme B12, cobamamide, and dibencozide, is, along with methylcobalamin (MeCbl), one of the biologically active forms of vitamin B12.

Adenosylcobalamin participates as a cofactor in radical-mediated 1,2-carbon skeleton rearrangements. These processes require the formation of the deoxyadenosyl radical through homolytic dissociation of the carbon-cobalt bond. This bond is exceptionally weak, with a bond dissociation energy of 31 kcal/mol, which is further lowered in the chemical environment of an enzyme active site. An enzyme that uses adenosylcobalamin as a cofactor is methylmalonyl-CoA mutase (MCM).

Further experimentation has also determined adenosylcobalamin's role in regulating expression of some bacterial genes. By binding to CarH, AdoCbl can modulate carotenoid genes, which confer warm colors onto various plants. Carotenoid transcription is activated by sunlight, due to the response from AdoCbl. There are other photoreceptors across different bacterial communities, aside from CarH, that also have reactive capability when bound to AdoCbl. For instance, AerR is another factor that uses AdoCbl to give off purple pigmentation. Additional examination of adenosylcobalamin-bound enzymes and the development of this cofactor over time may prove to hold regulatory function of DNA and RNA.

See also

External links