3D model (JSmol)
|Molar mass||202.35 g·mol−1|
|Density||937 mg mL−1|
|Melting point||28 to 30 °C (82 to 86 °F; 301 to 303 K)|
|Boiling point||150.1 °C; 302.1 °F; 423.2 K at 700 Pa|
|GHS signal word||DANGER|
|P280, P305+351+338, P310|
|Flash point||110 °C (230 °F; 383 K)|
|Spermidine, Putrescine, Cadaverine, Diethylenetriamine|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|what is ?)(|
Spermine is a polyamine involved in cellular metabolism found in all eukaryotic cells. The precursor for synthesis of spermine is the amino acid ornithine. 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 Antonie van Leeuwenhoek. The name spermin was first used by the German chemists Ladenburg and Abel in 1888, and the correct structure of spermine was not finally established until 1926, simultaneously in England (by Dudley, Rosenheim, and Starling) and Germany (by Wrede et al.). Spermine is the chemical primarily responsible for the characteristic odor of semen.
Spermine biosynthesis from animals starts from the conversion of L-Ornithine to putrescine by PLP and through two consecutive action of N-alkylation with decarboxylated SAM, spermine is synthesized. Plants have different routes to biosynthesize spermine. One of the route converts L-Glutamine to L-Ornithine and then L-Ornithine follows the same pathway as in animals to spermine.
Another pathway in plants starts from L-Arginine. It is first decarboxylated, followed by hydrolysis of the imine functional group in a guanidine system to produce N-carbamoylputrescine. Then N-carbamoylputrescine is hydrolyzed to produce putrescine with urea as a byproduct.
- 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.
- Ladenburg A., Abel J. (1888) Über das Aethylenimin (Spermin?). Ber. Dtsch. chem. Ges. 21: 758-766
- Dudley H. W., Rosenheim O., Starling W. W. (1926) The chemical constitution of spermine. III.Structure and synthesis. Biochemical Journal 20(5): 1082-1094
- Wrede F. (1925) Über die aus menschlichem Sperma isolierte Base Spermin. Dtsch. Med. Wochenschr. 51: 24
- Klein, David (2013). Organic Chemistry (2nd ed.).
- Porter, Carl W.; McManis, Jim; Casero, Robert A.; Bergeron, Raymond J. (1987). "Relative Abilities of Bis(ethyl) Derivatives of Putrescine, Spermidine, and Spermine to Regulate Polyamine Biosynthesis and Inhibit L1210 Leukemia Cell Growth" (PDF). Cancer Research. 47: 2821–2825.
- Pegg, Anthony E.; Wechter, Rita; Pakala, Rajbabu; Bergeron, Raymond J. (1989). "Effect of N1, N12-Bis(ethyl)spermine and Related Compounds on Growth and Polyamine Acetylation, Content, and Excretion in Human Colon Tumor Cells" (PDF). Journal of Biological Chemistry. 264 (20): 11744–11749.
- Dewick, Paul M (2009). Medicinal Natural Products: a biosynthetic approach (3rd ed.). Chichester U.K.: Wiley. p. 312. ISBN 9780470742761.