Cyanocobalamin Structure

Decoding the Structure of Cyanocobalamin: The B12 Vitamin

Vitamin B12, also known as cobalamin, plays a crucial role in various metabolic processes, including DNA synthesis, fatty acid metabolism, and the formation of myelin. This article aims to provide a detailed understanding of the structure of cyanocobalamin, the most common form of vitamin B12 used in supplements and pharmaceutical preparations. Understanding its structure provides insights into its function, bioavailability, and interactions within the body. We will explore the molecule's key components, their arrangement, and the implications of this unique structure.

I. The Corrin Ring: The Foundation of B12

At the heart of cyanocobalamin lies the corrin ring. This structure is similar to a porphyrin ring, found in heme (the iron-containing component of hemoglobin), but with a crucial difference: one methine bridge is missing. This results in a slightly puckered, non-planar structure. The corrin ring is composed of four pyrrole rings interconnected by methine bridges (=CH-), forming a ring system. This ring coordinates a central cobalt ion (Co³+), which is the key to B12's biological activity. The cobalt ion's oxidation state and the ligands bound to it determine the specific form of cobalamin.

II. Axial Ligands: Defining the Cyanocobalamin Variant

The cobalt ion in the corrin ring has two axial coordination sites – one above and one below the plane of the ring. These sites are occupied by ligands that significantly influence the molecule's properties. In cyanocobalamin, one axial position is occupied by 5,6-dimethylbenzimidazole (DMB), a nitrogenous base that's connected to the corrin ring through a ribose and a phosphate group forming a nucleotide-like structure. This creates a "lower" ligand connection which is essential for its interaction with enzymes. The other axial position is occupied by a cyanide ion (CN⁻), giving the molecule its name. It's important to note that other cobalamin forms, such as methylcobalamin (methyl group) and adenosylcobalamin (adenosine group), differ only in the nature of the ligand at this upper axial position.

III. The Role of the Nucleotide Loop: Intramolecular Interactions

The connection between the DMB base and the corrin ring is not simply a direct bond. It involves a ribose sugar and a phosphate group, creating a nucleotide-like loop that connects to the corrin ring. This loop isn't merely structural; it plays a vital role in the interaction of cobalamin with its enzymes. The loop can interact with the enzyme's binding pocket, orienting the cobalt and its axial ligand for optimal catalytic activity. For instance, in the case of methionine synthase, the precise orientation facilitated by the nucleotide loop is essential for the transfer of a methyl group from methylcobalamin to homocysteine.

IV. Structural Implications for Function

The unique structure of cyanocobalamin, particularly the corrin ring, the cobalt ion, and the axial ligands, is directly linked to its biological function as a coenzyme. The cobalt ion facilitates redox reactions, allowing the molecule to participate in crucial enzymatic processes. The specific ligand at the upper axial position dictates the type of reaction the cobalamin can catalyze. For example, adenosylcobalamin is essential for the enzyme methylmalonyl-CoA mutase, which is crucial for the metabolism of fatty acids.

V. Differences from Other Cobalamins

It’s crucial to understand that cyanocobalamin is a synthetic form of B12. While it’s readily absorbed and converted into other active forms within the body, some research suggests that methylcobalamin and adenosylcobalamin might be more readily utilized by the body. These forms naturally occur in foods and contain a methyl group or adenosyl group respectively instead of a cyanide ion at the upper axial position. The cyanide group is non-toxic at the concentrations found in B12 supplements, but some individuals prefer to avoid it.

Conclusion

The intricate structure of cyanocobalamin, characterized by the corrin ring, central cobalt ion, and axial ligands, is intrinsically linked to its biological function. Understanding this complex structure provides valuable insight into how B12 interacts with enzymes and contributes to essential metabolic pathways. While cyanocobalamin is a readily available and bioavailable form, further research continues to unravel the subtle differences in efficacy among various forms of cobalamin.

FAQs

1. Is cyanocobalamin safe? Yes, cyanocobalamin is generally considered safe at the dosages used in supplements, with the cyanide being released at very low and non-toxic levels.
2. What are the differences between cyanocobalamin and other B12 forms? They differ primarily in the ligand attached to the upper axial position of the cobalt ion, affecting how easily they're utilized by enzymes.
3. Can I convert cyanocobalamin to other active forms of B12? Yes, the body can efficiently convert cyanocobalamin to methylcobalamin and adenosylcobalamin.
4. Is cyanocobalamin suitable for vegans? Yes, as it is a synthetic form, it can be a reliable source of B12 for vegans.
5. What are the symptoms of B12 deficiency? Symptoms can range from fatigue and weakness to anemia, nerve damage, and cognitive impairment.

Search Results:

Cyanocobalamin (Vitamin B12) | C63H88CoN14O14P | CID … Cyanocobalamin (Vitamin B12) | C63H88CoN14O14P | CID 168432548 - structure, chemical names, physical and chemical properties, classification, patents, literature, biological activities, safety/hazards/toxicity information, supplier lists, and more.

Cyanocobalamin Structure - globaldatabase.ecpat.org This article aims to provide a detailed understanding of the structure of cyanocobalamin, the most common form of vitamin B12 used in supplements and pharmaceutical preparations. Understanding its structure provides insights into its function, bioavailability, and interactions within the body.

Cyanocobalamin vs. Hydroxocobalamin - What's the Difference? The structural difference between Cyanocobalamin and Hydroxocobalamin lies in the type of ligand attached to the cobalt atom. Cyanocobalamin has a cyanide ligand, while Hydroxocobalamin has a hydroxyl ligand. This structural variation can influence their absorption, metabolism, and overall efficacy within the body. Stability and Shelf Life

Cyanocobalamin - Wikipedia Cyanocobalamin is a form of vitamin B 12 used to treat and prevent vitamin B 12 deficiency except in the presence of cyanide toxicity. [7] [8] [2] The deficiency may occur in pernicious anemia, following surgical removal of the stomach, with fish tapeworm, or due to bowel cancer. [9] [5] It is used by mouth, by injection into a muscle, or as a ...

Structure cyanocobalamin - Big Chemical Encyclopedia As the name suggests, cyanocobalamin (vitamin B12) is a compound of cobalt (Co(lll)). With a complex organic structure, this essential water-soluble vitamin is obtained from dietary animal sources and is required for deoxyribonucleic acid (DNA) synthesis, where enzymes that use vitamin B12 are involved in the transfer of one-carbon units.

Cyanocobalamin: Functions & Deficiency | Vitamin B - Biology Properties and Distribution of Cyanocobalamin: Red crystalline substance, soluble in water. Contains metalloporphyrin nucleus and cobalt (4.5%). Molecular weight is 1,500 approximately. Distribution: Absent in plants, but present in almost all animal tissues.

Structures of cobalamins. Vitamin B 12 or cyanocobalamin … Adenosylcobalamin (AdoCbl), or coenzyme B12, is a cofactor for enzymes important in metabolism in humans (and other mammals) and bacteria. AdoCbl contains a Co-C bond and is extremely light...

Cyanocobalamin - NIST Chemistry WebBook Chemical structure: This structure is also available as a 2d Mol file; Permanent link for this species. Use this link for bookmarking this species for future reference. Information on this page: IR Spectrum; References; Notes; Other data available: Reaction thermochemistry data; Options: Switch to calorie-based units

Cyanocobalamin | C63H88CoN14O14P | CID 166596686 Cyanocobalamin is a cobalt -containing coordination compound generated by intestinal microbes, and a natural water -soluble vitamin of the B-complex family that must combine with Intrinsic Factor for absorption by the intestine.

Vitamin B12 - Wikipedia The structure of B 12 is based on a corrin ring, which is similar to the porphyrin ring found in heme. The central metal ion is cobalt . As isolated as an air-stable solid and available commercially, cobalt in vitamin B 12 (cyanocobalamin and …