Corrin is a

heterocyclic compound A heterocyclic compound or ring structure is a cyclic compound that has atoms of at least two different elements as members of its ring(s). Heterocyclic chemistry is the branch of organic chemistry dealing with the synthesis, properties, and ...

. It is the parent macrocycle related to the

substituted A substitution reaction (also known as single displacement reaction or single substitution reaction) is a chemical reaction during which one functional group in a chemical compound is replaced by another functional group. Substitution reactions ar ...

derivative that is found in vitamin B₁₂. Its name reflects that it is the "core" of vitamin B₁₂ (

cobalamin Vitamin B12, also known as cobalamin, is a water-soluble vitamin involved in metabolism. It is one of eight B vitamins. It is required by animals, which use it as a cofactor in DNA synthesis, in both fatty acid and amino acid metabolism. It ...

s).Nelson, D. L.; Cox, M. M. "Lehninger, Principles of Biochemistry" 3rd Ed. Worth Publishing: New York, 2000. . There are two chiral centres, which in natural compounds like cobalamin have the same stereochemistry.

Coordination chemistry

Upon deprotonation, the corrinoid ring is capable of binding

cobalt Cobalt is a chemical element with the symbol Co and atomic number 27. As with nickel, cobalt is found in the Earth's crust only in a chemically combined form, save for small deposits found in alloys of natural meteoric iron. The free element, pro ...

. In vitamin B₁₂, the resulting complex also features a benzimidazole-derived ligand, and the sixth site on the octahedron serves as the catalytic center. The corrin ring resembles the porphyrin ring, which occurs in hemoglobin. Both feature four

pyrrole Pyrrole is a heterocyclic aromatic organic compound, a five-membered ring with the formula C4 H4 NH. It is a colorless volatile liquid that darkens readily upon exposure to air. Substituted derivatives are also called pyrroles, e.g., ''N''-methy ...

-like subunits organized into a ring with a largely conjugated structure of alternating double and single bonds. In contrast to porphyrins, corrins lack one of the carbon groups that link the pyrrole-like units into a fully conjugated structure. With a conjugated system that extends only 3/4 of the way around the ring, and does not include any of the outer edge carbons, corrins have a number of non-conjugated sp³ carbons, making them more flexible than porphyrins and not as flat. A third closely related biological structure, the

chlorin In organic chemistry, chlorins are tetrapyrrole pigments that are partially hydrogenated porphyrins. The parent chlorin is an unstable compound which undergoes air oxidation to porphine. The name chlorin derives from chlorophyll. Chlorophylls ...

ring system found in

chlorophyll Chlorophyll (also chlorophyl) is any of several related green pigments found in cyanobacteria and in the chloroplasts of algae and plants. Its name is derived from the Greek words , ("pale green") and , ("leaf"). Chlorophyll allow plants to ...

, is intermediate between porphyrin and corrin, having 20 carbons like the porphyrins and a conjugated structure extending all the way around the central atom, but with only 6 of the 8 edge carbons participating.

Corrole A corrole is an aromatic tetrapyrrole. The corrin ring is also present in cobalamin ( vitamin B12). The ring consists of nineteen carbon atoms, with four nitrogen atoms in the core of the molecule. In this sense, corrole is very similar to porph ...

s (octadehydrocorrins) are fully

aromatic In chemistry, aromaticity is a chemical property of cyclic ( ring-shaped), ''typically'' planar (flat) molecular structures with pi bonds in resonance (those containing delocalized electrons) that gives increased stability compared to satu ...

derivatives of corrins.

References

{{Tetrapyrroles Biomolecules Tetrapyrroles Metabolism Macrocycles Schiff bases