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Adenylthiomethylpentose

Adenylthiomethylpentose
Adenylthiomethylpentose.svg
Names
IUPAC name
(2R',3R,4S,5S)-2-(6-Amino-9H-purin-9-yl)-5-[(methylsulfanyl)methyl]oxolane-3,4-diol
Other names
  • 5'-S-Methyl-5'-thioadenosine
  • 5'-(Methylthio)-5'-deoxyadenosine
  • 5'-(Methylthio)adenosine
  • 5'-Deoxy(methylthio)adenosine
  • 5'-Deoxy-5'-(methylthio)adenosine
  • 5'-S-Methylthioadenosine
  • 9'-(5-Thiomethyl-ribofuranosyl)-adenine
  • Vitamin L2
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.154.727
KEGG
PubChem CID
Properties
C11H15N5O3S
Molar mass 297.33 g·mol−1
Melting point 205 °C (401 °F; 478 K)
Hazards
Lethal dose or concentration (LD, LC):
LD50 (median dose)
>1000 mg/kg (mouse, oral)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Adenylthiomethylpentose is a sulfur-containing nucleoside that was formerly known as vitamin L2.

In 1912, an adenine nucleoside was isolated by Hunter et al. from yeast that were grown without phosphorus or sulfur. Later that substance was shown by Levene and Sobotkal to be adenylthiomethylpentose.

In 1936, W. Nakahara et al. did experiments on rats that suggested that vitamin L2 deficiency inhibits the ability of rats to lactate. In 1942 they identified vitamin L2 to be adenylthiomethylpentose. Later studies by Folley et al refuted Nakahara's claims and demonstrated that L2 is not necessary for lactation and thus L2 is not considered a vitamin today.

Hecht found in 1937 that the body temperature of rabbits, cats and guinea pigs were lowered by 1 to 2 degrees after he gave them adenylthiomethylpentose at a dose of 0.2 g/kg. Kühn et al. replicated this in guinea pigs in 1941.


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