Isoalloxazine

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Isoalloxazine
Alloxazine.svg
Names
IUPAC name
1H-benzo[g]pteridine-2,4-dione
Other names
1,2,3,4-Tetrahydrobenzopteridine-2,4-dione; Benzo(g)pteridine-2,4(1H,3H)-dione
Identifiers
3D model (JSmol)
85819
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.007.014 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 207-714-3
PubChem CID
UNII
  • InChI=1S/C10H6N4O2/c15-9-7-8(13-10(16)14-9)12-6-4-2-1-3-5(6)11-7/h1-4H,(H2,12,13,14,15,16)
    Key: HAUGRYOERYOXHX-UHFFFAOYSA-N
  • C1=CC=C2C(=C1)N=C3C(=N2)NC(=O)NC3=O
Properties
C10H6N4O2
Molar mass 214.184 g·mol−1
AppearanceRed solid
Melting point 200 °C (392 °F; 473 K) [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Isoalloxazine is the structural foundation of flavins such as riboflavin (vitamin B2) and is a heterocyclic compound. [2] It has a tricyclic structure which means it has three interconnected rings of atoms and is a tautomer of alloxazine. [1] The structure is formed by primary-secondary aromatic o-diamines and they are a high-melting crystalline substance. [1] The R-group is used to attach various flavin groups It has a similar structure to pteridines which has two interconnected rings. [1] Isoalloxazine was first obtained in 1934 [1] by Richard Kuhn an Austrian-German biochemist and lab mates.

Isoalloxazine Structure Isoalloxazine Structure.png
Isoalloxazine Structure

Isoalloxazine ring

Isoalloxazine rings can exist in different redox and ionization states depending on the chemistry of FMN and FAD associated with it. [3] Using the redox-active isoalloxazine system, FAD and FMN are able to do one and two electron transfer reactions and also be coupled with proton transfers. [4]

Ionization and redox states of the isoalloxazine ring Ionization and redox of isoalloxazine ring.png
Ionization and redox states of the isoalloxazine ring

References

  1. 1 2 3 4 5 Berezovskii, VM; Eremenko, TV (1963). "Chemistry of Alloxazines and Isoalloxazines". Russian Chemical Reviews. 32 (6): 290–307. doi:10.1070/RC1963v032n06ABEH001343 . Retrieved November 23, 2022.
  2. ↑ "isoalloxazine". Farlex Partner Medical Dictionary. 2012. Retrieved November 25, 2022.
  3. ↑ Luliano, James N. (2019). "Vibrational spectroscopy of flavoproteins". New Approaches for Flavin Catalysis. Methods in Enzymology. Vol. 620 (volume 620 ed.). Methods in Enzymology: Elsevier Inc. pp. 189–214. doi:10.1016/bs.mie.2019.03.011. ISBN   9780128168295. ISSN   0076-6879. PMID   31072487. S2CID   146800749.
  4. ↑ Aleksandrov, Alexey (2019). "A Molecular Mechanics Model for Flavins". Journal of Computational Chemistry. 40 (32): 2834–2842. doi:10.1002/jcc.26061. PMID   31471978. S2CID   201730443.
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