Hypoxanthine
IUPAC name	1H-purin-6(9H)-one
Identifiers
CAS number	68-94-0 Y
PubChem	790
MeSH	Hypoxanthine
SMILES	O=C1C2=C(NC=N2)N=CN1
Properties
Molecular formula	C5H4N4O
Molar mass	136.112
Y (what is this?)  (verify) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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 is also known as 6-Hydroxypurine. Hypoxanthine is a necessary additive in certain cell, bacteria and parasite cultures as a substrate and nitrogen source. For example 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.

[edit] Reactions

It is one of the products of the action of xanthine oxidase on xanthine, though more normally in purine degradation, hypoxanthine is formed from reduction of xanthine 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.

[edit] Additional images

Adenine. Notice the extra nitrogen compared to the oxygen in hypoxanthine. (Disregard the fact that the rings are in opposite positions.)

[edit] External links

• MeSH Hypoxanthine

v • d • e Nucleotide metabolic intermediates Purine metabolism Anabolism R5P→IMP: R5P · PRPP · PRA · GAR · FGAR · FGAM · AIR · CAIR · SAICAR · AICAR · FAICAR IMP→AMP: Adenylosuccinate IMP→GMP: Xanthosine monophosphate Catabolism Hypoxanthine · Xanthine · Uric acid · 5-Hydroxyisourate Pyrimidine metabolism Anabolism Carbamoyl phosphate · Carbamoyl aspartic acid · 4,5-Dihydroorotic acid · Orotic acid · Orotidine 5'-monophosphate · Uridine monophosphate Catabolism uracil: Dihydrouracil · 3-Ureidopropionic acid · β-Alanine thymine: Dihydrothymine · β-Ureidoisobutyric acid · 3-Aminoisobutyric acid see also enzymes, disorders

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