C3021

Dicyanocobinamide

≥93%

• Synonym(s): Cobinamide dicyanide, Etiocobalamin, Factor B
• Empirical Formula (Hill Notation): C₅₀H₇₂CoN₁₃O₈
• CAS Number: 27792-36-5
• Molecular Weight: 1042.12
• MDL number: MFCD00056330
• UNSPSC Code: 12352205
• PubChem Substance ID: 24892558
• NACRES: NA.79

Properties

• biological source: synthetic (organic)
• assay: ≥93%
• form: powder
• impurities: ≤0.1% vitamin B₁₂
• color: purple to very dark purple
• storage temp.: −20°C
• SMILES string: N#C[Co]C#N.C[C@H](O)CNC(=O)CC[C@]1(C)[C@@H](CC(N)=O)C2N=C1C(C)=C3N=C(C=C4N=C(C(C)=C5N[C@]2(C)[C@@](C)(CC(N)=O)[C@@H]5CCC(N)=O)[C@@](C)(CC(N)=O)[C@@H]4CCC(N)=O)C(C)(C)[C@@H]3CCC(N)=O
• InChI: 1S/C48H73N11O8.2CN.Co/c1-23(60)22-55-38(67)16-17-45(6)29(18-35(52)64)43-48(9)47(8,21-37(54)66)28(12-15-34(51)63)40(59-48)25(3)42-46(7,20-36(53)65)26(10-13-32(49)61)30(56-42)19-31-44(4,5)27(11-14-33(50)62)39(57-31)24(2)41(45)58-43;2*1-2;/h19,23,26-29,43,59-60H,10-18,20-22H2,1-9H3,(H2,49,61)(H2,50,62)(H2,51,63)(H2,52,64)(H2,53,65)(H2,54,66)(H,55,67);;;/b30-19-,39-24-,40-25-;;;/t23-,26+,27+,28+,29-,43?,45+,46-,47-,48-;;;/m0.../s1
• InChI key: NJATWHPHZUGTHR-GXEWULDJSA-N

Description

General description

Dicyanocobinamide, also known as factor b is a coenzyme B12 precursor. It has a corrin ring structure with four of the six coordination sites of the cobalt (Co) atom being the pyrrole nitrogen atoms.

Application

Dicyanocobinamide has been used for the crystallization of vitamin B₁₂-binding protein (BtuF). It has also been used for the destabilization of BtuCD-BtuF Interaction.

For use in determining non-intrinsic factor (R protein) in intrinsic factor preparations.

Biochem/physiol Actions

Dicyanocobinamide (Cbi) functions as a soluble guanylate cyclase (sGC) co-activator and targets the N-terminal regulatory regions. This action is similar to the effect of forskolin on adenylyl cyclases. Dicyanocobinamide elevates the intracellular cyclic guanosine monophosphate (cGMP) levels and exhibits vasorelaxant activity in rats. It is used along with various cobalamins in studies of the inhibition of HIV-1 integrase and nitric oxide synthase.

Safety Information

• pictograms: GHS07
• signalword: Warning
• hcodes: H302
• Hazard Classifications: Acute Tox. 4 Oral
• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable