Cyano-8-epicobalamin

• CAT Number: R028098
• CAS Number: 41325-63-7
• Molecular Formula: C₆₃H₈₈CoN₁₄O₁₄P
• Molecular Weight: 1355.37
• Purity: ≥95%
• Synonyms: (8β)-Cobinamide Cyanide 3’-Ester with 5,6-dimethyl-1-α-D-ribofuranosyl-1H-benzimidazole Dihydrogen Phosphate (ester), inner salt, 8-Epicobalamine; 8-epi-Cyanocobalamin; Cyanocobalamin Impurity H
• Storage: Desiccate at -20C
• IUPAC Name: cobalt(3+);[(2R,3S,4R,5S)-5-(5,6-dimethylbenzimidazol-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl] [(2R)-1-[3-[(2R,3R,4Z,7S,9Z,12R,13S,14Z,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;cyanide
• InChI: InChI=1S/C62H90N13O14P.CN.Co/c1-29-20-39-40(21-30(29)2)75(28-70-39)57-52(84)53(41(27-76)87-57)89-90(85,86)88-31(3)26-69-49(83)18-19-59(8)37(22-46(66)80)56-62(11)61(10,25-48(68)82)36(14-17-45(65)79)51(74-62)33(5)55-60(9,24-47(67)81)34(12-15-43(63)77)38(71-55)23-42-58(6,7)35(13-16-44(64)78)50(72-42)32(4)54(59)73-56;1-2;/h20-21,23,28,31,34-37,41,52-53,56-57,76,84H,12-19,22,24-27H2,1-11H3,(H15,63,64,65,66,67,68,69,71,72,73,74,77,78,79,80,81,82,83,85,86);;/q;-1;+3/p-2/t31-,34+,35-,36-,37+,41-,52-,53-,56?,57+,59-,60+,61+,62+;;/m1../s1
• InChIKey: FDJOLVPMNUYSCM-KYGGNWNPSA-L
• SMILES: 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](C5[C@]6([C@@]([C@@H](C(=N6)/C(=C\7/[C@@]([C@H](C(=N7)/C=C\8/C([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.[C-]#N.[Co+3]

Cyano-8-epicobalamin(CAT: R028098) is a synthetic analog of vitamin B₁₂ (cobalamin) in which the cobalt-bound upper axial ligand is a cyano group (–CN) and the configuration at the C-8 position of the corrin ring is epimerized. This structural modification leads to altered biochemical activity and receptor interactions, making it a valuable probe in vitamin B₁₂ metabolism, transport, and enzyme cofactor studies. While it does not function as a typical coenzyme B₁₂ in metabolic pathways, cyano-8-epicobalamin is instrumental in exploring structure–function relationships and the biological specificity of cobalamin-dependent enzymes. It is also used in pharmaceutical research and mechanistic enzymology.