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Hypoxanthine

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Title: Hypoxanthine  
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Subject: Nucleobase, Xanthine oxidase, Inosine, Purine metabolism, Purinones
Collection: Purines
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Hypoxanthine

Hypoxanthine
Names
IUPAC name
1H-purin-6(9H)-one
Identifiers
 Y
ChEBI  Y
ChEMBL  Y
ChemSpider  Y
Jmol-3D images Image
KEGG  Y
MeSH
PubChem
UNII  Y
Properties
C5H4N4O
Molar mass 136.112
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
 Y  (: Y/N?)

Hypoxanthine is a naturally occurring purine derivative. It is occasionally found as a constituent of nucleic acids, where it is present in the anticodon of tRNA in the form of its nucleoside inosine. It has a tautomer known as 6-hydroxypurine. Hypoxanthine is a necessary additive in certain cell, bacteria, and parasite cultures as a substrate and nitrogen source. For example,[1] it is commonly a required reagent in malaria parasite cultures, since Plasmodium falciparum requires a source of hypoxanthine for nucleic acid synthesis and energy metabolism.

In August 2011, a report, based on DNA and RNA components adenine and guanine, may have been formed extraterrestrially in outer space.[2][3][4]

The Pheretima aspergillum worm, used in Chinese medicine preparations, contains hypoxanthine.[5]

Contents

  • Reactions 1
  • Additional images 2
  • References 3
  • External links 4

Reactions

It is one of the products of the action of xanthine oxidase on xanthine. However, more frequently in purine degradation, xanthine is formed from reduction of hypoxanthine by xanthine oxidoreductase.

Hypoxanthine-guanine phosphoribosyltransferase converts hypoxanthine into IMP in nucleotide salvage.

Hypoxanthine is also a spontaneous deamination product of adenine. Because of its resemblance to guanine, the spontaneous deamination of adenine can lead to an error in DNA transcription/replication.

Additional images

References

  1. ^ "3H-hypoxanthine uptake inhibition assay for drug susceptibility".  
  2. ^ Callahan; Smith, K.E.; Cleaves, H.J.; Ruzica, J.; Stern, J.C.; Glavin, D.P.; House, C.H.; Dworkin, J.P. (11 August 2011). "Carbonaceous meteorites contain a wide range of extraterrestrial nucleobases".  
  3. ^ Steigerwald, John (8 August 2011). "NASA Researchers: DNA Building Blocks Can Be Made in Space".  
  4. ^ ScienceDaily Staff (9 August 2011). "DNA Building Blocks Can Be Made in Space, NASA Evidence Suggests".  
  5. ^ The Pharmacology of Chinese Herbs, Second Edition By Kee C. Huang

External links

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