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5′-Methylthioadenosine

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5′-Methylthioadenosine
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 Edit this at Wikidata
KEGG
  • InChI=1S/C11H15N5O3S/c1-20-2-5-7(17)8(18)11(19-5)16-4-15-6-9(12)13-3-14-10(6)16/h3-5,7-8,11,17-18H,2H2,1H3,(H2,12,13,14)/t5-,7-,8-,11-/m1/s1
    Key: WUUGFSXJNOTRMR-IOSLPCCCSA-N
  • InChI=1/C11H15N5O3S/c1-20-2-5-7(17)8(18)11(19-5)16-4-15-6-9(12)13-3-14-10(6)16/h3-5,7-8,11,17-18H,2H2,1H3,(H2,12,13,14)/t5-,7-,8-,11-/m1/s1
    Key: WUUGFSXJNOTRMR-IOSLPCCCBD
  • CSC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C(N)N=CN=C12
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):
>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).

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 2017-01-28).{{cite journal}}: CS1 maint: DOI inactive as of January 2017 (link)
  8. ^ Waro Nakahara; Fumito Inukai; 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; S. K. Kon (1942). "Lactation and Reproduction on Highly Purified Diets". Nature. 150 (3802): 318. Bibcode:1942Natur.150Q.318F. doi:10.1038/150318a0.
  10. ^ R. Kuhn u. K. Henkel (1941). "Über die Senkung der Körpertemperatur durch Adenylthiomethylpentose". Biological Chemistry. 269 (1): 41–46. doi:10.1515/bchm2.1941.269.1.41.
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