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Concept
Methylcobalamin
Summary
Methylcobalamin (mecobalamin, MeCbl, or MeB_12) is a cobalamin, a form of vitamin B_12. It differs from cyanocobalamin in that the cyano group at the cobalt is replaced with a methyl group. Methylcobalamin features an octahedral cobalt(III) centre and can be obtained as bright red crystals. From the perspective of coordination chemistry, methylcobalamin is notable as a rare example of a compound that contains metal–alkyl bonds. Nickel–methyl intermediates have been proposed for the final step of methanogenesis.
Methylcobalamin is equivalent physiologically to vitamin B_12, and can be used to prevent or treat pathology arising from a lack of vitamin B_12 intake (vitamin B12 deficiency).
Methylcobalamin is also used in the treatment of peripheral neuropathy, diabetic neuropathy, and as a preliminary treatment for amyotrophic lateral sclerosis.
Methylcobalamin that is ingested is not used directly as a cofactor, but is first converted by MMACHC into cob(II)alamin. Cob(II)alamin is then later converted into the other two forms, adenosylcobalamin and methylcobalamin for use as cofactors. That is, methylcobalamin is first dealkylated and then regenerated.
According to one author, it is important to treat vitamin B_12 deficiency with hydroxocobalamin or cyanocobalamin or a combination of adenosylcobalamin and methylcobalamin, and not methylcobalamin alone.
TOC
Methylcobalamin can be produced in the laboratory by reducing cyanocobalamin with sodium borohydride in alkaline solution, followed by the addition of methyl iodide.
Dolphin D. [205] Preparation of the reduced forms of vitamin B12 and of some analogs of the vitamin B12 coenzyme containing a cobalt-carbon bond. . .
This vitamer, along with adenosylcobalamin, is one of two active coenzymes used by vitamin B_12-dependent enzymes and is the specific vitamin B_12 form used by 5-methyltetrahydrofolate-homocysteine methyltransferase (MTR), also known as methionine synthase.
Methylcobalamin participates in the Wood-Ljungdahl pathway, which is a pathway by which some organisms utilize carbon dioxide as their source of organic compounds.
Official source
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