Xanthosine

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Xanthosine[1]
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Names
IUPAC name
Xanthosine[2]
Systematic IUPAC name
9-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3,9-dihydro-1H-purine-2,6-dione
Other names
Xanthine riboside; 9-β-D-Ribofuranosylxanthine
Identifiers
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3D model (JSmol)
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  • InChI=1S/C10H12N4O6/c15-1-3-5(16)6(17)9(20-3)14-2-11-4-7(14)12-10(19)13-8(4)18/h2-3,5-6,9,15-17H,1H2,(H2,12,13,18,19)/t3-,5-,6-,9-/m1/s1 checkY
    Key: UBORTCNDUKBEOP-UUOKFMHZSA-N checkY
  • C1=NC2=C(N1[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O)NC(=O)NC2=O
  • O=C3Nc1c(ncn1[C@@H]2O[C@@H]([C@@H](O)[C@H]2O)CO)C(=O)N3
Properties
C10H12N4O6
Molar mass 284.228 g·mol−1
Melting point Decomposes when heated
Sparingly soluble in cold water; freely soluble in hot water
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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Xanthosine is a nucleoside derived from xanthine and ribose. It is the biosynthetic precursor to 7-methylxanthosine by the action of 7-methylxanthosine synthase. 7-Methylxanthosine in turn is the precursor to theobromine (active alkaloid in chocolate), which in turn is the precursor to caffeine, the alkaloid in coffee and tea.[3][4]

See also

References

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  1. ^ Merck Index, 11th Edition, 9974
  2. ^ Page Module:Citation/CS1/styles.css has no content.International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 1421. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.
  3. ^ Page Module:Citation/CS1/styles.css has no content.Ashihara, Hiroshi; Yokota, Takao; Crozier, Alan (2013). Biosynthesis and catabolism of purine alkaloids. Advances in Botanical Research. Vol. 68. pp. 111–138. doi:10.1016/B978-0-12-408061-4.00004-3. ISBN 978-0-12-408061-4.
  4. ^ Page Module:Citation/CS1/styles.css has no content.Uefuji, Hirotaka; Ogita, Shinjiro; Yamaguchi, Yube; Koizumi, Nozomu; Sano, Hiroshi (2003). "Molecular Cloning and Functional Characterization of Three Distinct N -Methyltransferases Involved in the Caffeine Biosynthetic Pathway in Coffee Plants". Plant Physiology. 132 (1): 372–380. doi:10.1104/pp.102.019679. PMC 166982. PMID 12746542.

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