Spermine

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Spermine
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IUPAC name N,N'-bis(3-aminopropyl) butane-1,4-diamine
Other names gerontine, musculamine and neuridine
Identifiers
CAS number 71-44-3
PubChem 1103
MeSH Spermine
SMILES C(CCNCCCN)CNCCCN
Properties
Molecular formula C10H26N4
Molar mass 202.34
Density 0.937 g/cm3
Melting point

29°C

Boiling point

130 °C

Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

Spermine is a polyamine involved in cellular metabolism found in all eukaryotic cells. Formed from spermidine, it is found in a wide variety of organisms and tissues and is an essential growth factor in some bacteria. It is found as a polycation at physiological pH. Spermine is associated with nucleic acids and is thought to stabilize helical structure, particularly in viruses.

Crystals of spermine phosphate were first described in 1678, in human semen, by Anton van Leeuwenhoek[1]. The name spermin [sic] was first used by the German chemists Ladenburg and Abel in 1888[2], and the correct structure of spermine was not finally established until 1926, simultaneously in England (by Dudley, Rosenheim, and Starling)[3] and Germany (by Wrede. et al)[4].

See also

References

Notes

  1. Leeuwenhoek, A. van (1678) Observationes D. Anthonii Leeuwenhoek, de natis e semine genitali animalculis. Letter dated November 1677. Philos. Trans. Roy. Soc. London, 12,1040-1043.
  2. Ladenburg A., Abel J. (1888) Über das Aethylenimin (Spermin?). Ber. Dtsch. chem. Ges. 21: 758-766
  3. Dudley H. W., Rosenheim O., Starling W. W. (1926) The chemical constitution of spermine. III.Structure and synthesis. Biochemical Journal 20(5): 1082-1094
  4. Wrede F. (1925) Über die aus menschlichem Sperma isolierte Base Spermin. Dtsch. Med. Wochenschr. 51: 24

General references



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