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The parent of porphyrins is porphine, a rare chemical compound of exclusively theoretical interest. Substituted porphines are called porphyrins. [1] With a total of 26 π-electrons, of which 18 π-electrons form a planar, continuous cycle, the porphyrin ring structure is often described as aromatic.
The porphyrin with a core phosphorus (V) ion can be tuned with additional substituents added to either the outside of the polycyclic ring system or axially to the core phosphorus. Meso-substituted porphyrins like meso-tetra-p-tolylporphyrin (TTP) and octaethylporphyrin (OEP) are often used in synthesis of the core phosphorus porphyrin.
In coordination chemistry, a macrocyclic ligand is a macrocyclic ring having at least nine atoms (including all hetero atoms) and three or more donor sites that serve as ligands. [1] Crown ethers and porphyrins are prominent examples. Macrocyclic ligands often exhibit high affinity for metal ions, the macrocyclic effect.
Pyrrole is another compound made up of molecules with a five-membered heterocyclic ring. These molecules are unsaturated and contain a nitrogen atom in the ring. Four pyrrole rings are joined in a ring structure called a porphyrin. The rings of porphyrin are components of hemoglobin, myoglobin, vitamin B12, chlorophyll, and cytochromes.
The general term protoporphyrin refers to porphine derivatives that have the outer hydrogen atoms in the four pyrrole rings replaced by other functional groups. The prefix proto often means 'first' in science nomenclature (such as carbon protoxide), hence Hans Fischer is thought to have coined the name protoporphyrin as the first class of porphyrins. [3]
The molecule is a flat macrocycle, consisting of four pyrrole-like rings joined by four methine bridges, which makes it the simplest of the tetrapyrroles. [1] The nonpolar tetrapyrrolic ring structure of porphine means it is poorly soluble in most organic solvents and hardly water soluble. [2] As a result, porphine is mostly of theoretical ...
Porphyrins, including heme, the core of hemoglobin; Chlorins, including those at the core of chlorophyll. Cyclic tetrapyrroles having three one-carbon bridges and one direct bond between the pyrroles include: Corrins, including the cores of cobalamins, when complexed with a cobalt ion.
The porphyrin ring is a planar dianionic, tetradentate ligand. The iron is typically Fe 2+ or Fe 3+. One or two ligands are attached at the axial sites. The porphyrin ring has 4 nitrogen atoms that bind to the iron, leaving two other coordination positions of the iron available for bonding to the histidine of the protein and a divalent atom. [2]