# Corrin

> Mediated Wiki article. Canonical URL: https://mediated.wiki/source/Corrin
> Markdown URL: https://mediated.wiki/source/Corrin.md
> Source: https://en.wikipedia.org/wiki/Corrin
> Source revision: 1298135623
> License: Creative Commons Attribution-ShareAlike 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/)

{{Other uses|Corrin (disambiguation)}}
{{Chembox
| verifiedrevid  = 443543138
| ImageFile      = Corrin.svg
| ImageSize      = 220px
| IUPACName      = (5''Z'',9''Z'',14''Z'')-2,3,7,8,12,13,17,18,19,22-Decahydro-1''H''-corrin<ref>https://pubchem.ncbi.nlm.nih.gov/compound/6438343#section=IUPAC-Name&fullscreen=true</ref>
| OtherNames     = 
| Section1       = {{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 16736705
| InChIKey = WUPRCGRRQUZFAB-DEGKJRJSBL
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C19H22N4/c1-3-14-10-16-5-7-18(22-16)19-8-6-17(23-19)11-15-4-2-13(21-15)9-12(1)20-14/h9-11,18-19,22H,1-8H2/b12-9-,15-11-,16-10-
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = WUPRCGRRQUZFAB-DEGKJRJSSA-N
| CASNo_Ref = {{cascite|correct|??}}
| CASNo=262-76-0
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 288E04GRMT
| PubChem=6438343
| InChI = 1/C19H22N4/c1-3-14-10-16-5-7-18(22-16)19-8-6-17(23-19)11-15-4-2-13(21-15)9-12(1)20-14/h9-11,18-19,22H,1-8H2/b12-9-,15-11-,16-10-
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 33221
| SMILES = N=1C=4CCC=1\C=C2/NC(CC2)C\5CC/C(C=C3\CC/C(=N3)/C=4)=N/5
}}
| Section2       = {{Chembox Properties
| Formula=C<sub>19</sub>H<sub>22</sub>N<sub>4</sub>
| MolarMass=306.40478
| Appearance=
| Density=
| MeltingPt=
| BoilingPt=
| Solubility=
  }}
| Section3       = {{Chembox Hazards
| MainHazards=
| FlashPt=
| AutoignitionPt =
  }}
}}
'''Corrin''' is a [heterocyclic compound](/source/heterocyclic_compound).  Although not known to exist on its own, the molecule is of interest as the parent [macrocycle](/source/macrocycle) related to the cofactor and [chromophore](/source/chromophore) in [vitamin B<sub>12</sub>](/source/vitamin_B12). Its name reflects that it is the "core" of [vitamin B<sub>12</sub>](/source/vitamin_B12) ([cobalamin](/source/cobalamin)s). Compounds with a corrin core are known as "corrins".<ref>Nelson, D. L.; Cox, M. M. "Lehninger, Principles of Biochemistry" 3rd Ed. Worth Publishing: New York, 2000. {{ISBN|1-57259-153-6}}.</ref>

There are two [chiral centre](/source/chiral_centre)s, which in natural compounds like cobalamin have the same [stereochemistry](/source/stereochemistry).

==Coordination chemistry==
{{main|vitamin B12|l1=Vitamin B<sub>12</sub>}}
Upon deprotonation, the corrinoid ring is capable of binding [cobalt](/source/cobalt).  In vitamin B<sub>12</sub>, 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](/source/porphyrin) ring.<ref>{{cite journal |doi=10.1021/cr030720z|title=Chemistry and Enzymology of Vitamin B12 |year=2005 |last1=Brown |first1=Kenneth L. |journal=Chemical Reviews |volume=105 |issue=6 |pages=2075–2150 |pmid=15941210 }}</ref>  Both feature four [pyrrole](/source/pyrrole)-like subunits organized into rings.  Corrins have a central 15-membered {{chem2|C11N4}} ring whereas porphyrins have an interior 16-membered {{chem2|C12N4}} ring. All four nitrogen centers are linked by [conjugation](/source/Conjugated_system) structure, with alternating double and single bonds.  In contrast to [porphyrin](/source/porphyrin)s, 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 sp<sup>3</sup> carbons, making them more flexible than porphyrins and not as flat.   A third closely related biological structure, the [chlorin](/source/chlorin) ring system found in [chlorophyll](/source/chlorophyll), 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](/source/Corrole)s (octadehydrocorrins) are fully [aromatic](/source/aromatic) derivatives of corrins.

==References==
{{reflist}}

== Further reading ==
* {{cite journal |last1=Kieninger |first1=Christoph |last2=Deery |first2=Evelyne |last3=Lawrence |first3=Andrew D. |last4=Podewitz |first4=Maren |last5=Wurst |first5=Klaus |last6=Nemoto‐Smith |first6=Emi |last7=Widner |first7=Florian J. |last8=Baker |first8=Joseph A. |last9=Jockusch |first9=Steffen |last10=Kreutz |first10=Christoph R. |last11=Liedl |first11=Klaus R. |last12=Gruber |first12=Karl |last13=Warren |first13=Martin J. |last14=Kräutler |first14=Bernhard |title=The Hydrogenobyric Acid Structure Reveals the Corrin Ligand as an Entatic State Module Empowering B 12 Cofactors for Catalysis |journal=Angewandte Chemie International Edition |date=29 July 2019 |volume=58 |issue=31 |pages=10756–10760 |doi=10.1002/anie.201904713|pmid=31115943 |pmc=6771967 }}

{{Tetrapyrroles}}

Category:Biomolecules
Category:Tetrapyrroles
Category:Metabolism
Category:Macrocycles
Category:Schiff bases

---
Adapted from the Wikipedia article [Corrin](https://en.wikipedia.org/wiki/Corrin) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Corrin?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.