Hypoxanthine

Source: Wikipedia, the free encyclopedia.
Hypoxanthine
Names
Preferred IUPAC name
1,9-Dihydro-6H-purin-6-one
Identifiers
3D model (
JSmol
)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard
 100.000.634 Edit this at Wikidata
IUPHAR/BPS
KEGG
MeSH Hypoxanthine
UNII
  • InChI=1S/C5H4N4O/c10-5-3-4(7-1-6-3)8-2-9-5/h1-2H,(H2,6,7,8,9,10) checkY
    Key: FDGQSTZJBFJUBT-UHFFFAOYSA-N checkY
  • InChI=1/C5H4N4O/c10-5-3-4(7-1-6-3)8-2-9-5/h1-2H,(H2,6,7,8,9,10)
    Key: FDGQSTZJBFJUBT-UHFFFAOYAJ
  • c1[nH]c2c(n1)[nH]cnc2=O
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).
checkY verify (what is checkY☒N ?)

Hypoxanthine is a naturally occurring

tRNA in the form of its nucleoside inosine. It has a tautomer known as 6-hydroxypurine. Hypoxanthine is a necessary additive in certain cells, bacteria, and parasite cultures as a substrate and nitrogen source. For example,[1][2] 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

organic molecules, including the DNA and RNA components adenine and guanine, may have been formed extraterrestrially in outer space.[3][4][5]

The Pheretima aspergillum worm, used in Chinese medicine preparations, contains hypoxanthine.[6]

Reactions

It is one of the products of the action of

xanthine oxidoreductase
.

IMP in nucleotide salvage
.

Hypoxanthine is also a spontaneous

DNA transcription/replication, as it base pairs with cytosine
. Hypoxanthine is removed from DNA by base excision repair, initiated by N-methylpurine glycosylase (MPG), also known as alkyl adenine glycosylase (Aag). [7]

Additional images

References

  1. ^ "Estimation of Plasmodium falciparum drug susceptibility by the 3H-hypoxanthine uptake inhibition assay" (PDF). Worldwide Antimalarial Resistance Network. Archived (PDF) from the original on 2022-10-09. Retrieved 2017-01-20.
  2. PMID 11132385
    .
  3. PMID 21836052
    .
  4. ^ Steigerwald, John (8 August 2011). "NASA Researchers: DNA Building Blocks Can Be Made in Space". NASA. Retrieved 2011-08-10.
  5. ^ ScienceDaily Staff (9 August 2011). "DNA Building Blocks Can Be Made in Space, NASA Evidence Suggests". ScienceDaily. Retrieved 2011-08-09.
  6. ^ The Pharmacology of Chinese Herbs, Second Edition By Kee C. Huang
  7. PMID 19219989
    .

External links
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