Pyrrole in the context of "Heme group"

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⭐ Core Definition: Pyrrole

Pyrrole is a heterocyclic, aromatic, organic compound, a five-membered ring with the formula C4H4NH. It is a colorless volatile liquid that darkens readily upon exposure to air. Substituted derivatives are also called pyrroles, e.g., N-methylpyrrole, C4H4NCH3. Porphobilinogen, a trisubstituted pyrrole, is the biosynthetic precursor to many natural products such as heme.

Pyrroles are components of more complex macrocycles, including the porphyrinogens and products derived therefrom, including porphyrins of heme, the chlorins, bacteriochlorins, and chlorophylls.

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👉 Pyrrole in the context of Heme group

Heme (American English), or haem (Commonwealth English, both pronounced /hi:m/ HEEM), is a ring-shaped iron-containing molecule that serves as a ligand of various proteins, especially as a component of hemoglobin, which carries oxygen in the bloodstream. It is composed of four pyrrole rings with two vinyl and two propionic acid side chains. Heme is biosynthesized in both the bone marrow and the liver.

Heme plays a critical role in several redox reactions in mammals, due to its ability to carry the oxygen molecule. Reactions include oxidative metabolism (cytochrome c oxidase, succinate dehydrogenase), xenobiotic detoxification via cytochrome P450 pathways (including metabolism of some drugs), gas sensing (guanyl cyclases, nitric oxide synthase), and microRNA processing (DGCR8).

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Pyrrole in the context of Porphyrin

Porphyrins (/ˈpɔːrfərɪns/ POR-fər-ins) are heterocyclic, macrocyclic, organic compounds, composed of four modified pyrrole subunits interconnected at their α carbon atoms via methine bridges (=CH−). In vertebrates, an essential member of the porphyrin group is heme, which is a component of hemoproteins, whose functions include carrying oxygen in the bloodstream. In plants, an essential porphyrin derivative is chlorophyll, which is involved in light harvesting and electron transfer in photosynthesis.

The parent of porphyrins is porphine, a rare chemical compound of exclusively theoretical interest. Substituted porphines are called porphyrins. With a total of 26 π-electrons the porphyrin ring structure is a coordinated aromatic system. One result of the large conjugated system is that porphyrins absorb strongly in the visible region of the electromagnetic spectrum, i.e. they are deeply colored. The name "porphyrin" derives from Greek πορφύρα (porphyra) 'purple'.

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Pyrrole in the context of Porphine

Porphine or porphin is an organic compound of empirical formula C20H14N4. It is heterocyclic and aromatic. 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.

The nonpolar tetrapyrrolic ring structure of porphine means it is poorly soluble in most organic solvents and hardly water soluble. As a result, porphine is mostly of theoretical interest. It has been detected in GC-MS of certain fractions of Piper betle.

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