5′-Methylthioadenosine
Chemical compound
From Wikipedia, the free encyclopedia
5′-Methylthioadenosine is S-methyl derivative of the adenosine. It is an intermediate in the methylthioadenosine (MTA) cycle, also known as the methionine salvage pathway, that is universal to aerobic organisms.[3][4]
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| Names | |
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| IUPAC name
5′-S-Methyl-5′-thioadenosine | |
| Systematic IUPAC name
(2R,3R,4S,5S)-2-(6-Amino-9H-purin-9-yl)-5-[(methylsulfanyl)methyl]oxolane-3,4-diol | |
Other names
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| Identifiers | |
3D model (JSmol) |
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| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.154.727 |
| KEGG | |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C11H15N5O3S | |
| Molar mass | 297.33 g·mol−1 |
| Melting point | 205 °C (401 °F; 478 K)[1] |
| Hazards | |
| Lethal dose or concentration (LD, LC): | |
LD50 (median dose) |
>1000 mg/kg (mouse, oral)[2] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Formation
The pervasive cofactor S-adenosyl methionine (SAM) is the precursor to 5′-methylthioadenosine. The sulfonium group in SAM can cleave in three ways, one involves loss of CH2CH2CH(NH3+)CO2−, generating the title compound.
History
In 1912, an adenine nucleoside was isolated by Hunter et al. from yeast that were grown without phosphorus or sulfur.[5] Later in 1925, that substance was shown by Levene and Sobotkal to be adenylthiomethylpentose.[6]
In 1936, Nakahara et al. did experiments on rats that suggested that vitamin L2 deficiency inhibits the ability of female rats for lactation.[7] In 1942, they identified vitamin L2 to be adenylthiomethylpentose.[8] Later studies by Folley et al (1942) refuted Nakahara's claims and demonstrated that L2 is not necessary for lactation and thus L2 is not considered a vitamin today.[9]
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 this biochemical at a dose of 0.2 g/kg. Kühn et al. replicated this in guinea pigs in 1941.[10]