methylcobalamin

Also known as benexol, mecobalamin, MeCbl, MeB12

Methylcobalamin (mecobalamin, MeCbl, or MeB) is a cobalamin, a form of vitamin B. 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.

Chemical data

Formula: C63H91CoN13O14P
Molecular weight: 1344.4 g/mol
IUPAC name: carbanide;cobalt(3+);[(2R,3S,4R,5S)-5-(5,6-dimethylbenzimidazol-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl] [(2S)-1-[3-[(1R,2R,3R,7S,12S,13S,17S,18S,19R)-2,13,18-tris(2-amino-2-oxoethyl)-7,12,17-tris(3-amino-3-oxopropyl)-3,5,8,8,13,15,18,19-octamethyl-2,7,12,17-tetrahydro-1H-corrin-21-id-3-yl]propanoylamino]propan-2-yl] phosphate
SMILES: [CH3-].CC1=CC2=C(C=C1C)N(C=N2)[C@@H]3[C@@H]([C@@H]([C@H](O3)CO)OP(=O)([O-])O[C@@H](C)CNC(=O)CC[C@@]4([C@H]([C@@H]5[C@]6([C@@]([C@@H](C(=N6)C(=C7[C@@]([C@@H](C(=N7)C=C8C([C@@H](C(=N8)C(=C4[N-]5)C)CCC(=O)N)(C)C)CCC(=O)N)(C)CC(=O)N)C)CCC(=O)N)(C)CC(=O)N)C)CC(=O)N)C)O.[Co+3]
InChIKey: ZFLASALABLFSNM-QBOHGLHMSA-L
Polar surface area: 452 Å²
H-bond donors: 9
H-bond acceptors: 20
Formal charge: 0

via PubChem

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Encyclopedic overview

6 sections

Contents

Production
Functions
Role in human health
Research directions
See also
References

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Excerpted from Wikipedia’s “methylcobalamin” article, available under the CC BY-SA 4.0 licence.

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