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C3021

Sigma-Aldrich

Dicyanocobinamide

≥93%

Synonym(s):

Cobinamide dicyanide, Etiocobalamin, Factor B

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About This Item

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

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

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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.

pictograms

Exclamation mark
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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Conformational change of a tryptophan residue in BtuF facilitates binding and transport of cobinamide by the vitamin B12 transporter BtuCD-F
Mireku SA, et al.
Scientific reports, 7, 41575-41575 (2017)
The Different Effects of Substrates and Nucleotides on the Complex Formation of ABC Transporters
Fiorentino F, et al.
Structure, 27(4), 651-659 (2019)
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