6,7-Dimethyl-8-ribityllumazine

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6,7-Dimethyl-8-ribityllumazine
6,7-dimethyl-8-ribityllumazine.svg
Names
IUPAC name
8-(1-Deoxy-D-ribitol-1-yl)-6,7-dimethylpteridine-2,4(3H,8H)-dione
Systematic IUPAC name
6,7-Dimethyl-8-[(2S,3S,4R)-2,3,4,5-tetrahydropentyl]pteridine-2,4(3H,8H)-dione
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
MeSH 6,7-dimethyl-8-ribityllumazine
PubChem CID
UNII
  • InChI=1S/C13H18N4O6/c1-5-6(2)17(3-7(19)10(21)8(20)4-18)11-9(14-5)12(22)16-13(23)15-11/h7-8,10,18-21H,3-4H2,1-2H3,(H,16,22,23)/t7-,8+,10-/m0/s1 Yes check.svgY
    Key: SXDXRJZUAJBNFL-XKSSXDPKSA-N Yes check.svgY
  • InChI=1/C13H18N4O6/c1-5-6(2)17(3-7(19)10(21)8(20)4-18)11-9(14-5)12(22)16-13(23)15-11/h7-8,10,18-21H,3-4H2,1-2H3,(H,16,22,23)/t7-,8+,10-/m0/s1
    Key: SXDXRJZUAJBNFL-XKSSXDPKBB
  • O=C2/N=C\1/N(\C(=C(/N=C/1C(=O)N2)C)C)C[C@H](O)[C@H](O)[C@H](O)CO
Properties
C13H18N4O6
Molar mass 326.305 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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6,7-Dimethyl-8-ribityllumazine is a precursor for riboflavin. [1] [2] It is acted upon by riboflavin synthase.

References

  1. Maley, Gladys F.; Plaut, G. W. E. (1959-04-01). "THE CONVERSION OF 6,7-DIMETHYL-8-RIBITYLLUMAZINE (6,7-DIMETHYL-8-RIBITYL-2,4[1H,3H]-PTERIDINEDIONE) TO RIBOFLAVIN BY EXTRACTS OF ASHBYA GOSSYPII". Journal of the American Chemical Society. 81 (8): 2025–2025. doi:10.1021/ja01517a062. ISSN   0002-7863.
  2. Kis, Klaus; Kugelbrey, Karl; Bacher, Adelbert (2001-04-01). "Biosynthesis of Riboflavin. The Reaction Catalyzed by 6,7-Dimethyl-8-ribityllumazine Synthase Can Proceed without Enzymatic Catalysis under Physiological Conditions†". The Journal of Organic Chemistry. 66 (8): 2555–2559. doi:10.1021/jo001120s. ISSN   0022-3263.