Adenylthiomethylpentose

Adenylthiomethylpentose

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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
CAS Number	2457-80-9
Jmol 3D model	Interactive image
SMILES CSC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C(N)N=CN=C12
Properties
Chemical formula	C11H15N5O3S
Molar mass	297.33 g·mol−1
Melting point	205 °C (401 °F; 478 K)
Vapor pressure	{{{value}}}
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.