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Isoalloxazine

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Isoalloxazine
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 Edit this at Wikidata
EC Number
  • 207-714-3
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
Appearance Red 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 ring

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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

References

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  1. ^ a b c d e 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.