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Chemical compound
Spermine is a polyamine involved in cellular metabolism that is found in all eukaryotic cells. The precursor for synthesis of spermine is the amino acid ornithine. It is an essential growth factor in some bacteria as well. 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. It functions as an intracellular free radical scavenger to protect DNA from free radical attack.[1] Spermine is the chemical primarily responsible for the characteristic odor of semen.[2]
Antonie van Leeuwenhoek first described crystals of spermine phosphate in human semen in 1678.[3] The name spermin was first used by the German chemists Ladenburg and Abel in 1888,[4][5] and the correct structure of spermine was not finally established until 1926, simultaneously in England (by Dudley, Rosenheim, and Starling)[6][7] and Germany (by Wrede et al.).[8]
^Ha, Hyo Chol; Sirisoma, Nilantha S.; Kuppusamy, Periannan; Zweier, Jay L.; Woster, Patrick M.; Casero, Robert A. (1998-09-15). "The natural polyamine spermine functions directly as a free radical scavenger". PNAS. 95 (19): 11140–11145. doi:10.1073/pnas.95.19.11140. ISSN 0027-8424. PMC 21609. PMID 9736703.
^
Klein, David (2013). Organic Chemistry (2nd ed.).
^Lewenhoeck, D. A (1677). "Observationes D. Anthonii Lewenhoeck, De Natis E Semine Genitali Animalculis". Philosophical Transactions of the Royal Society of London. 12 (133–142): 1040–1046. Bibcode:1677RSPT...12.1040A. doi:10.1098/rstl.1677.0068.
^Ladenburg, A; Abel, J (1888). "Ueber das Aethylenimin (Spermin?)". Berichte der Deutschen Chemischen Gesellschaft. 21: 758–766. doi:10.1002/cber.188802101139.
^Ladenburg, A; Abel, J (1888). "Nachtrag zu der Mittheilung über das Aethylenimin". Berichte der Deutschen Chemischen Gesellschaft. 21 (2): 2706. doi:10.1002/cber.18880210293.
^Dudley, H. W; Rosenheim, O; Starling, W. W (1926). "The Chemical Constitution of Spermine: Structure and Synthesis". Biochemical Journal. 20 (5): 1082–1094. doi:10.1042/bj0201082. PMC 1251823. PMID 16743746.
^Dudley, Harold Ward; Rosenheim, Mary Christine; Rosenheim, Otto (1924). "The Chemical Constitution of Spermine. I. The Isolation of Spermine from Animal Tissues, and the Preparation of its Salts". Biochemical Journal. 18 (6): 1263–72. doi:10.1042/bj0181263. PMC 1259516. PMID 16743399.
^Wrede, F (2009). "Ueber die aus dem menschlichen Sperma isolierte Base Spermin". Deutsche Medizinische Wochenschrift. 51: 24. doi:10.1055/s-0028-1136345.
Spermine is a polyamine involved in cellular metabolism that is found in all eukaryotic cells. The precursor for synthesis of spermine is the amino acid...
The principal examples are the triamine spermidine and the tetraamine spermine. They are structurally and biosynthetically related to the diamines putrescine...
Spermine synthase (EC 2.5.1.22, spermidine aminopropyltransferase, spermine synthetase) is an enzyme that converts spermidine into spermine. This enzyme...
Spermine oxidase (EC 1.5.3.16, PAOh1/SMO, AtPAO1, AtPAO4, SMO) is an enzyme with systematic name spermidine:oxygen oxidoreductase (spermidine-forming)...
formation from putrescine. It is a precursor to other polyamines, such as spermine and its structural isomer thermospermine. Spermidine synchronizes an array...
Histamine and adenosine were detected at 0.14% and 0.10% with the polyamine spermine noted in trace amounts at 0.002% (Moore et al., 2009). A female (left)...
is combined with another S-adenosylmethioninamine and gets converted to spermine. Putrescine is synthesized in small quantities by healthy living cells...
grams (0.95 oz) of pure putrescine. For comparison the similar substance spermine, found in semen, is over 3 times as toxic. Neurine "Mass burials do more...
Medicine. Coleman CS, Stanley BA, Jones AD, Pegg AE (Nov 2004). "Spermidine/spermine-N1-acetyltransferase-2 (SSAT2) acetylates thialysine and is not involved...
oligonucleotides after automated synthesis. A mixture of 5-methoxysalicylic acid and spermine can be used as a matrix for oligonucleotides analysis in MALDI mass spectrometry...
Willems, M.I. (1997). "Acute and subacute toxicity of tyramine, spermidine, spermine, putrescine and cadaverine in rats". Food and Chemical Toxicology. 35 (3–4):...
compensate for this hostile environment. Basic amines such as putrescine, spermine, spermidine and cadaverine are responsible for the smell and flavor of...
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