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Molecules 2006, 11(7), 539-548; doi:10.3390/11070539
Article

A Novel Biosurfactant, 2-Acyloxyethylphosphonate, Isolated from Waterblooms of Aphanizomenon flos-aquae

1,* , 2
,
2,* , 2
,
3
,
3
 and
1
1 Graduate School of Environmental Studies, Tohoku University, Aoba-ku, Sendai 980-8579, Japan 2 Division of Environmental and Applied Biology, School of Life Sciences, University of Dundee, Dundee DD1 4HN, UK 3 National Institute for Environmental Studies, 16-2 Onogawa, Tsukuba Ibaraki 305-8506, Japan
* Authors to whom correspondence should be addressed.
Received: 16 June 2006 / Revised: 18 July 2006 / Accepted: 18 July 2006 / Published: 22 July 2006
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Abstract

A novel biosurfactant, 2-acyloxyethylphosphonate, was isolated from waterblooms of Aphanizomenon flos-aquae. Its structure was elucidated by chemical degradation and HRFABMS, GC/EI-MS and 1D- and 2D-NMR spectral analyses. The surfactant contained one mole of 2-hydroxyethylphosphonate and one mole of fatty acid, with hexadecanoic acid accounting for 84.1% of the total fatty acid content. The structure was confirmed by synthesis of 2-oleoyloxyethylphosphonate from ethylene oxide, phosphorus acid and oleic acid chloride. Considering the isolated surfactant molecule as hexadecanoyloxyethylphosphonic acid (mw. 364), the critical micelle concentration (CMC) was about 22 mM.
Keywords: biosurfactant; cyanobacterium; Aphanizomenon flos-aquae; fatty acids; 2-hydroxyethanephosphonate; 2-acyloxyethanephosphonate; C-P linkage; surface tension; toxicity; critical micelle concentration (CMC). biosurfactant; cyanobacterium; Aphanizomenon flos-aquae; fatty acids; 2-hydroxyethanephosphonate; 2-acyloxyethanephosphonate; C-P linkage; surface tension; toxicity; critical micelle concentration (CMC).
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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Kaya, K.; Morrison, L.F.; Codd, G.A.; Metcalf, J.S.; Sano, T.; Takagi, H.; Kubo, T. A Novel Biosurfactant, 2-Acyloxyethylphosphonate, Isolated from Waterblooms of Aphanizomenon flos-aquae. Molecules 2006, 11, 539-548.

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