Adenylthiomethylpentose

Adenylthiomethylpentose

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)[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).
Infobox references

Adenylthiomethylpentose is a sulfur-containing nucleoside^[3] that was formerly known as vitamin L₂.^[4]

In 1912, an adenine nucleoside was isolated by Hunter et al. from yeast that were grown without phosphorus or sulfur.^[5] Later that substance was shown by Levene and Sobotkal to be adenylthiomethylpentose.^[6]

In 1936, W. Nakahara et al. did experiments on rats that suggested that vitamin L₂ deficiency inhibits the ability of rats to lactate.^[7] In 1942 they identified vitamin L₂ to be adenylthiomethylpentose.^[8] 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.^[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 adenylthiomethylpentose at a dose of 0.2 g/kg. Kühn et al. replicated this in guinea pigs in 1941.^[10]

References

1. Baddiley, J. (1951). "The synthesis of pantothenic acid-2′ and -4′ phosphates as possible degradation products of coenzyme A". Journal of the Chemical Society: 1348–1351. doi:10.1039/JR9510000246.
2. JP 04046124, Shimohashi, Hirotaka, issued 1992 
3. Satoh, Kiyoo; Makino, Katashi (1951). "Structure of Adenylthiomethylpentose". Nature 167 (4241): 238. Bibcode:1951Natur.167..238S. doi:10.1038/167238a0.
4. Michael W. Davidson. "Anthranilic Acid (Vitamin L)".
5. J. A. Mandel u. E. K. Dunham (1912). "Preliminary note on a purine-hexose compound". J. Biol. Chem. 11: 85.
6. P. A. Levene u. H. Sobotka (1925). "The thio-sugar from yeast" (PDF). J. Biol. Chem. 65: 551.
7. Waro Nakahara, Fumito Inukai, Saburo Ugami (1936). "Factor L2, a Second Dietary Factor for Lactation". Proceedings of the Imperial Academy 12 (9): 289–291. doi:10.2183/pjab1912.12.289 (inactive 2016-04-05).
8. Waro Nakahara, Fumito Inukai, and Saburo Ugami (1942). "Adenylthiomethylpentose as a Form of Vitamin L₂". Proceedings of the Imperial Academy 18 (8): 477–478.
9. S. J. Folley, K. M. Henry and S. K. Kon (1942). "Lactation and Reproduction on Highly Purified Diets". Nature 150: 318. doi:10.1038/150318a0.
10. R. Kuhn u. K. Henkel (1941). "Über die Senkung der Körpertemperatur durch Adenylthiomethylpentose". Biological Chemistry 269 (1).