Chemistry:Norspermidine
From HandWiki
Norspermidine is a polyamine of similar structure to the more common spermidine. Norspermidine has been found to occur naturally in some species of plants,[1][2] bacteria,[3] and algae.[4]
Norspermidine is being researched for use as a cancer medication.[5][6]
Biosynthesis
Norspermidine is an aliphatic polyamine. In ϵ-proteobacteria, which are found in human gut microbiota, a combination of two enzymes is used to produce norspermidine from 1,3-diaminopropane.[7] First, carboxynorspermidine synthase catalyses a reductive amination using nicotinamide adenine dinucleotide phosphate (NADPH) as the reducing agent.[8][9]
The intermediate, carboxynorspermidine, is then decarboxylated by carboxynorspermidine decarboxylase:[7][9]
References
- ↑ Rodriguez-Garay, B (1989). "Detection of Norspermidine and Norspermine in Medicago sativa L. (Alfalfa)". Plant Physiology 89 (2): 525–529. doi:10.1104/pp.89.2.525. ISSN 0032-0889. PMID 16666576.
- ↑ Hamana, K (1998). "Unusual polyamines in aquatic plants: the occurrence of homospermidine, norspermidine, thermospermine, norspermine, aminopropylhomospermidine, bis(aminopropyl)ethanediamine, and methylspermidine". Can. J. Bot. 76 (1): 130–133. doi:10.1139/cjb-76-1-130.
- ↑ Yamamoto, S (Apr 27, 1979). "Occurrence of norspermidine in some species of genera Vibrio and Beneckea". Biochem Biophys Res Commun 87 (4): 1102–1108. doi:10.1016/S0006-291X(79)80021-2. PMID 313792.
- ↑ Hamana, K; Matsuzaki, S (1982). "Widespread Occurrence of Norspermidine and Norspermine in Eukaryotic Algae". J. Biochem. 91 (4): 1321–1328. doi:10.1093/oxfordjournals.jbchem.a133818. ISSN 0021-924X. PMID 7096289.
- ↑ Prakash, NJ (1988). "Antitumor activity of norspermidine, a structural homologue of the natural polyamine spermidine". Anticancer Res. 8 (4): 563–568. PMID 3140710.
- ↑ Sunkara, PS (1988). "Mechanism of antitumor activity of norspermidine, a structural homologue of spermidine". Progress in Polyamine Research. Adv Exp Med Biol. 250. pp. 707–716. doi:10.1007/978-1-4684-5637-0_62. ISBN 978-1-4684-5639-4.
- ↑ 7.0 7.1 "Alternative spermidine biosynthetic route is critical for growth of Campylobacter jejuni and is the dominant polyamine pathway in human gut microbiota". The Journal of Biological Chemistry 286 (50): 43301–12. December 2011. doi:10.1074/jbc.M111.307835. PMID 22025614.
- ↑ "Purification and some properties of carboxynorspermidine synthase participating in a novel biosynthetic pathway for norspermidine in Vibrio alginolyticus". Journal of General Microbiology 137 (7): 1737–42. July 1991. doi:10.1099/00221287-137-7-1737. PMID 1955861.
- ↑ 9.0 9.1 "An alternative polyamine biosynthetic pathway is widespread in bacteria and essential for biofilm formation in Vibrio cholerae". The Journal of Biological Chemistry 284 (15): 9899–907. April 2009. doi:10.1074/jbc.M900110200. PMID 19196710.
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