Bilane
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| Names | |
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| IUPAC name
5,10,15,22,23,24-Hexahydro-21H-biline
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| Systematic IUPAC name
11H,31H,51H,71H-1,7(2),3,5(2,5)-Tetrapyrrolaheptaphane | |
| Other names
Bilinogen; Tetrapyrrolotrismethane
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| Identifiers | |
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3D model (JSmol)
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| 8008279 | |
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PubChem CID
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| Properties | |
| C19H20N4 | |
| Molar mass | 304.397 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Template:Chembox Footer/trackingTemplate:Short description
In organic chemistry, bilane is a compound with the formula Page Module:Chem2/styles.css has no content.C19H20N4 or Page Module:Chem2/styles.css has no content.[(C4H4N)−CH2−(C4H3N)−]2CH2. It is a tetrapyrrole, a class of compounds with four independent pyrrole rings. Specifically, the molecule can be described as four pyrrole molecules Page Module:Chem2/styles.css has no content.C4H5N connected in an open chain by three methylene bridges Page Module:Chem2/styles.css has no content.−CH2− at carbons adjacent to the nitrogens, replacing the respective hydrogens.[1]
The name is also used for the class of compounds formally derived from bilane proper by replacement of some additional hydrogen atoms by various functional groups. Natural bilanes usually have side chains substituted on the two carbons in each pyrrole ring that are not adjacent to the nitrogens. Artificial bilanes may be substituted on the bridging carbons (called meso positions).[2]
The parent (unsubstituted) bilane is difficult to prepare and unstable,[3] but substituted derivatives are synthesized by most living organisms as intermediates in the synthesis of natural porphyrins. Substituted bilanes may also be the starting point for the synthesis of artificial porphyrins.[2][3]
Reactions
Upon treatment with aldehydes, bilanes may cyclize to give porphyrinogens and various open or closed oligomers and polymers.[2]
In living organisms, the biosynthesis of all natural porphyrins proceeds through the bilane, hydroxymethylbilane, which is produced from four molecules of the monomer porphobilinogen, and then converted to the closed tetrapyrrole uroporphyrinogen III (or, in certain metabolic disorders, into uroporphyrinogen I).[4]
Also, the catabolism of hemoglobin in humans produces bilirubin, another linear tetrapyrrole that is a partially oxidized bilane.[5]
References
- ^ Page Module:Citation/CS1/styles.css has no content.Gerard P. Moss (1988). "Nomenclature of Tetrapyrroles. Recommendations 1986". European Journal of Biochemistry. 178 (2): 277–328. doi:10.1111/j.1432-1033.1988.tb14453.x. PMID 3208761.
- ^ a b c Page Module:Citation/CS1/styles.css has no content.Lindsey, J. S. (2010). "Synthetic Routes to meso-Patterned Porphyrins". Accounts of Chemical Research. 43 (2): 300–311. doi:10.1021/ar900212t. PMID 19863076.
- ^ a b Claudia Ryppa, Mathias O. Senge, Sabine S. Hatscher, Erich Kleinpeter, Philipp Wacker, Uwe Schilde, and Arno Wiehe (2005): "Synthesis of Mono- and Disubstituted Porphyrins: A- and 5,10-A2-Type Systems". Chemistry, A European Journal, volume 11, issue 11, pages 3427-3442. Script error: No such module "CS1 identifiers".
- ^ Page Module:Citation/CS1/styles.css has no content.Battersby, Alan R. (2000). "Tetrapyrroles: The pigments of life". Natural Product Reports. 17 (6): 507–526. doi:10.1039/b002635m. PMID 11152419.
- ^ Page Module:Citation/CS1/styles.css has no content.Vasavda C, Kothari R, Malla AP, Tokhunts R, Lin A, Ji M, et al. (October 2019). "Bilirubin Links Heme Metabolism to Neuroprotection by Scavenging Superoxide". Cell Chemical Biology. 26 (10): 1450–1460.e7. doi:10.1016/j.chembiol.2019.07.006. PMC 6893848. PMID 31353321.
