Bacterial Glycolipids
Part 5. Polysaccharides
Dr. Jitendra D. Desai,
Prof. Dr. Anjana J. Desai,
Dr. Jitendra D. Desai
- [email protected]
- +91-265-794396 | Fax: +91-265-270414
Indian Petrochemicals Corp. Ltd., P.O. Petrochemicals, Department of Environment and Ecology, Vadodara, Gujarat, India, 391 346
Search for more papers by this authorProf. Dr. Anjana J. Desai
- [email protected]
- +91-265-794396 | Fax: +91-265-792508
M. S. University of Baroda, Department of Microbiology and Biotechnology Center, Faculty of Science, Vadodara, Gujarat, India, 390 002
Search for more papers by this authorDr. Jitendra D. Desai,
Prof. Dr. Anjana J. Desai,
Dr. Jitendra D. Desai
- [email protected]
- +91-265-794396 | Fax: +91-265-270414
Indian Petrochemicals Corp. Ltd., P.O. Petrochemicals, Department of Environment and Ecology, Vadodara, Gujarat, India, 391 346
Search for more papers by this authorProf. Dr. Anjana J. Desai
- [email protected]
- +91-265-794396 | Fax: +91-265-792508
M. S. University of Baroda, Department of Microbiology and Biotechnology Center, Faculty of Science, Vadodara, Gujarat, India, 390 002
Search for more papers by this authorFirst published: 15 January 2005
Abstract
- Introduction
- Historical Outline
- Occurrence
- Chemical Structure
- Glycosyl Diglycerides
- Rhamnolipids
- Trehalolipids
- Complex Glycolipids
- Physiological Functions
- Biosynthesis
- Biodegradation
- Genetics and Regulation
- Production
- Fermentative Production
- Production by Biotransformation and Chemical Synthesis
- Recovery and Purification
- Applications
- Patents
- World Market and Cost Economics
- Outlook and Perspectives
- Acknowledgments
References
- Arcos, J. A., Bernabe, M., Otero, C. (1998) Different strategies for selective monoacylation of hexoaldoses in acetone, J. Surf. Detergents 1, 345–352.
- Arino, S., Marchal, R., Vandecasteele, J. P. (1998) Production of new extracellular glycolipids by a strain of Cellulomonas cellulans (Oerskovia xenthineolytica) and their structural characterization, Can J. Microbiol. 44, 238–243.
- Atlas, R. M. (1981) Microbial degradation of petroleum hydrocarbons: an environmental perspective, Microbiol. Rev. 45, 180–209.
- Asselineau, C., Asselineau, J. (1978) Trehalose containing glycolipids, Prog. Chem. Fats Lipids 16, 59–99.
- Babu, P. S., Vaidya, A. N., Bal, A. S., Kapur, R., Juwarkar, A., Khanna, P. (1996) Kinetics of biosurfactant production by Pseudomonas aeruginosa strain BS2 from industrial wastes, Biotechnol. Lett. 18, 263–268.
- Bai, G., Brusseau, M. L., Miller, R. M. (1997) Biosurfactant-enhanced removal of residual hydrocarbon from soil, J. Contamin. Hydrol. 25, 157–170.
- Banat, I. M., Samarah, N., Murad, M., Horne, R., Benerjee, S. (1991) Biosurfactant production and use in oil tank clean-up, World J. Microbiol. Biotechnol. 7, 80–84.
- Banat, I. M. (1995) Biosurfactants production and possible uses in microbial enhanced oil recovery and oil pollution remediation – a review, Bioresource Technol. 51, 1–12.
- Batrakov, S. G., Rozynov, B. V., Koronelli, T. V., Bergelson, L. D. (1981) Two novel types of trehaloselipids, Chem. Phys. Lipids 29, 241–266.
- Bertrand, J. C., Bonin, P., Goutx, M., Gauthier, M., Mille, G. (1994) The potential application of biosurfactants in combating hydrocarbon pollution in marine environment, Res. Microbiol. 145, 53–56.
-
Betts, K. S.
(1997)
Biosurfactants remove metals from soil,
Environ. Sci. Technol. 31,
547–548.
10.1021/es972588o Google Scholar
- Boulton, C. A., Ratledge, C. (1987) Biosynthesis of lipid precursors to surfactant production, in: Biosurfactants and Biotechnology ( N. Kosaric, W. L. Cairns, N. C. C. Gray, Eds.), Marcel Dekker, New York, 47–87.
- Brandenburg, K., Seydel, U. (1998) Infrared spectroscopy of glycolipids, Chem. Phys. Lipids 96, 23–40.
- Brennan, P. J., Lehane, D. P., Thomas, D. W. (1970) Acylglucoses of the Corynebacteria and Mycobacteria, Eur. J. Biochem. 13, 117–12.
- Bryant, F. O. (1990) Improved method for the isolation of biosurfactant glycolipids from Rhodococcus sp. strain H13A, Appl. Environ. Microbiol. 56, 1494–1496.
- Bunster, L., Fokkema, N. J., Schippers, B. (1989) Effect of surface-active Pseudomonas spp. on leaf wettability, Appl. Environ. Microbiol. 55, 1340–1345.
- Bush, C. A., Martin Pastor, M., Imborty, A. (1999) Structure and conformation of complex carbohydrates of glycoproteins, glycolipids and bacterial polysaccharides, Annu. Rev. Biophys. Biomol. Struct. 28, 269–278.
- Chameotra, S. S., Singh, H. D. (1990) Purification and characterization of alkane solubilizing factor produced by Pseudomonas sp. PG-1, J. Ferment. Bioeng. 69, 341–344.
- Cooper, D. G., Goldenberg, B. G. (1987) Surface active agents from two Bacillus species, Appl. Environ. Microbiol. 53, 224–229.
- Daniel, H. J., Otto, T. T., Binder, M., Reuss, M., Syldatk, C. (1998) Sophorolipid production with high yields on whey concentrated and rapeseed oil without consumption of lactose, Biotechnol. Lett. 20, 805–807.
- Davila, A. M., Marchal, R., Vandecasteele, J. P. (1997) Sophorose lipid fermentation with differentiated substrate supply for growth and production phases, Appl. Microbiol. Biotechnol. 47, 496–501.
- Desai, A. J., Patel, K. M., Desai, J. D. (1988) Emulsifier production by Pseudomonas fluorescens during the growth on hydrocarbons, Curr. Sci. 57, 500–501.
- Desai, J. D., Desai, A. J. (1993) Production of biosurfactants, in: Biosurfactants, Production, Properties, Applications ( N. Kosaric, Ed.), Marcel Dekker, New York, 65–97.
- Desai, J. D., Banat, I. M. (1997) Microbial production of surfactants and their commercial potential, Microbiol. Mol. Biol. Rev. 61, 47–64.
- Deziel, E., Paquette, G., Villemur, R., Lepine, F., Bisaillon, J. (1996) Biosurfactant production by soil Pseudomonas strain growing on polycyclic aromatic hydrocarbons, Appl. Environ. Microbiol. 62, 1908–1912.
- Duvnjak, Z., Cooper, D. G., Kosaric, N. (1983) Effect of nitrogen source on surfactant production by Arthrobacter paraffines ATCC 19558, in: Microbial Enhanced Oil Recovery ( J. E. Zajic, D. G. Cooper, T. R. Jack, N. Kosaric, Eds.), Pennwell, Tulsa, OK, 66–72.
-
Duynstee, H. I.,
Vliet, M. J.,
Marel, G. A.,
Boom, J. H.
(1998)
An efficient synthesis of (R)-3-{(R)-3-[2-O-(α-l-rhamnopyranosyl)-α-l-rhamnopyranosyl] oxydecanoyl} oxydecanoic acid, a rhamnolipid from Pseudomonas aeruginosa,
Eur. J. Org. Chem. 1998,
303–307.
10.1002/(SICI)1099-0690(199802)1998:2<303::AID-EJOC303>3.0.CO;2-U Google Scholar
- Edward, J. R., Hayashi, J. A. (1965) Structure of a rhamnolipid from Pseudomonas aeruginosa, Arch. Biochem. Biophys. 111, 415–421.
- Espuny, M. J., Ejido, S., Rodon, I., Manresa, A., Mercade, M. E. (1996) Nutritional requirements of a biosurfactant producing strain Rhodococcus sp. 51T7, Biotechnol. Lett. 18, 521–526.
- Fiechter, A. (1992) Biosurfactants, moving towards industrial application, Trends Biotechnol. 10, 208–217.
- Finnerty, W. R. (1994) Biosurfactants in environmental biotechnology, Curr. Opin. Biotechnol. 5, 291–295.
- Finnerty, W. R., Singer, M. E. (1985) A microbial biosurfactant physiology, Biochemistry and applications, Dev. Ind. Microbiol. 25, 31–46.
- Fregapane, G., Sarney, D. B., Greenberg, S. G., Knight, D. J., Vulfson, E. N. (1994) Enzymatic synthesis of monosaccharide fatty acid esters and their comparison with conventional products, J. Am. Chem. Soc. 71, 87–91.
- Glaser, L., Konfeld, S. (1966) Formation of dTDP-l-rhamnose from dTDP-d-glucose, Methods Enzymol. 8, 303–306.
- Guerra-Santos, L. H., Kappeli, O., Fiechter, A. (1986) Dependence of Pseudomonas aeruginosa continuous culture biosurfactant production on nutritional and environmental factors, Appl. Microbiol. Biotechnol. 24, 443–448.
- Haba, E., Espuny, M. J., Busquets, M., Manresa, A. (2000) Screening and production of rhamnolipids by Pseudomonas aeruginosa 47 T2 NCB 40044 from waste frying oils, J. Appl. Microbiol. 88, 379–387.
- Haferburg, D., Hommel, R., Kleber, H. P., Kluge, S., Schuster, G., Zschiegner, H. J. (1987) Antiphytovirale Aktivitat von Rhamnolipid aus Pseudomonas aeruginosa, Acta Biotechnol. 7, 353–356.
- Hardegger, M., Koch, A. K., Ochsner, U. A., Fiechter, A., Reiser, J. (1994) Cloning and heterologous expression of a gene encoding an alkane induced extracellular protein involved in alkane assimilation from Pseudomonas aeruginosa, Appl. Environ. Microbiol. 60, 3679–3687.
-
Harvey, D. J.
(1999)
Matrix-assisted laser-desorption ionization mass spectroscopy of carbohydrates,
Mass Spectrosc. Rev. 18,
349–450.
10.1002/(SICI)1098-2787(1999)18:6<349::AID-MAS1>3.0.CO;2-H CAS PubMed Web of Science® Google Scholar
- Harvey, S., Elashvili, I., Valdes, J. J., Kamely, D., Chakrabarty, A. M. (1990) Enhanced removal of Exxon Valdez spilled oil from Alaskan gravel by a microbial surfactant, Bio/Technology 8, 228–230.
- Hauser, G., Karnovsky, M. L. (1954) Studies on the production of glycolipid by Pseudomonas aeruginosa, J. Bacteriol. 68, 645–654.
- Hirayama, T., Kato, I. (1982) Novel rhamnolipids from Pseudomonas aeruginosa, FEBS Lett. 139, 81–85.
- Hommel, R. K. (1994) Formation and function of biosurfactants for degradation of water insoluble substrates, in: Biochemistry of Microbial Degradation ( C. Ratledge, Ed.), London: Kluwer, 63–87.
- Hommel, R. K., Ratledge, C. (1993) Biosynthetic mechanisms of low molecular weight surfactants and their precursor molecules, in: Biosurfactants, Production, Properties, Applications ( N. Kosaric, Ed.), Marcel Dekker, New York, 3–63.
- Ikada, I., Klibanov, A. M. (1993) Lipase catalyzed acylation of sugars solubilized in hydrophobic solvents by complexation, Biotechnol. Bioeng. 42, 788–791.
- Ishigami, Y., Gama, Y., Ishli, F., Kook, C. Y. (1993) Colloid chemical effect of polar head moieties of a rhamnolipid type biosurfactant, Langmuir 9, 1634–1636.
- Itoh, S., Suzuki, T. (1972) Effect of rhamnolipids on growth of Pseudomonas aeruginosa mutant deficient in n-paraffin utilizing ability, Agric. Biol. Chem. 36, 2233–2235.
- Itoh, S., Suzuki, T. (1974) Fructose lipids of Arthrobacter, Corynebacteria, Nocardia and Mycobacteria grown on fructose, Agric. Biol. Chem. 38, 1443–1449.
- Jain, D. K., Thompson, D. L. C., Lee, H., Trevors, J. T. (1991) A drop-collapsing test for screening surfactant producing microorganisms, J. Microbiol. Methods 13, 271–279.
- Jarvis, F. G., Johnson, M. J. (1949) A glycolipid produced by Pseudomonas aeruginosa, J. Am. Chem. Soc. 71, 4124–4126.
- Kim, J. S., Powalla, M., Lang, S., Wagner, F., Lunsdorf, H., Wrey, V. (1990) Microbial glycolipid production under nitrogen limitation and resting cell conditions, J. Biotechnol. 13, 257–266.
- Koch, A. K., Reiser, J., Kappeli, O., Fiechter, A. (1988) Genetic construction of lactose-utilizing stains of Pseudomonas aeruginosa and their application in biosurfactant production, Bio/Technology 6, 1335–1339.
- Koch, A. K., Kappeli, O., Fiechter, A., Reiser, J. (1991) Hydrocarbon assimilation and biosurfactant production in Pseudomonas aeruginosa mutants, J. Bacteriol. 173, 4212–4219.
- Kretschmer, A., Wagner, F. (1983) Characterization of biosynthetic intermediates of trehalose dimycolate from Rhodococcus erythropolis grown on n-alkanes, Biochim. Biophys. Acta 753, 306–313.
- Kretschmer, A., Bock, H., Wagner, F. (1982) Chemical and physical characterisation of interfacial-active lipids from Rhodococcus erythropolis grown on n-alkane, Appl. Environ. Microbiol. 44, 864–870.
- Lang, S. (1999) Production of microbial glycolipids, in: Methods in Biotechnology ( C. Bucke, Ed.), Humana Press, Totowa, NJ, 103–118.
- Lang, S., Philp, J. (1998) Surface active lipids in Rhodococcus, Antonie van Leeuwenhoek. 74, 59–70.
- Lang, S., Wagner, F. (1987) Structure and properties of biosurfactants, in: Biosurfactants and biotechnology ( N. Kosaric, W. L. Cairns, N. C. C. Gray, Eds.), Marcel Dekker, New York, 21–47.
- Lang, S., Wagner, F. (1993) Biological activities of biosurfactants, in: Biosurfactants, Production, Properties, Applications ( N. Kosaric, Ed.), Marcel Dekker, New York, 251–268.
- Lang, S., Wullbrandt, D. (1999) Rhamnose lipids – biosynthesis, microbial production and application potential, Appl. Microbiol. Biotechnol. 51, 22–32.
- Li, Z. Y., Lang, S., Wagner, F., Witte, L., Wray, V. (1984) Formation and identification of interfacial-active glycolipids from resting microbial cells of Arthrobacter sp. and potential use in tertiary oil recovery, Appl. Environ. Microbiol. 48, 610–617.
- Matsuyama, T., Sogawa, M., Yano, I. (1991) Direct colony thin layer chromatography and rapid characterization of S. marcescens mutants defective in production of wetting agents, Appl. Environ. Microbiol. 53, 1186–1188.
- Mattei, G., Rambeloarisoa, E., Giusti, G., Rontani, J. F., Bertrand, J. C. (1986) Fermentation procedure of a crude oil in continuous culture on seawater, Appl. Microbiol. Biotechnol. 23, 302–304.
- McClure, C. D., Schiller, N. L. (1992) Effect of Pseudomonas aeruginosa rhamnolipids on human monocyte derived macrophages, J. Leukoc. Biol. 51, 97–102.
- Mercade, M. E., Espuny, M. J., Manresa, A. (1997) The use of oil substrate for biosurfactant production, Recent Res. Dev. Oil. Chem. 1, 177–185.
- Mercade, M. E., Manresa, M. A. (1994) The use of agro industrial byproducts for biosurfactant production, J. Am. Oil. Chem. Soc. 71, 61–64.
- Mercade, M. E., Manresa, M. A., Robert, M., Espuny, M. J., de Andres, C., Guinea, J. (1993) Olive oil mill effluent (OOME) new substrate for biosurfactant production, Bioresource Technol. 43, 1–6.
- Miller, R. M. (1995) Biosurfactant-facilitated remediation of metal-contaminated soils, Environ. Health Perspect. 103, 59–62.
- Miller, R. M., Zhang, Y. (1997) Measurement of biosurfactant enhanced solubilization and biodegradation of hydrocarbons, Methods Biotechnol. 2, 59–66.
- Muller-Hurtig, R., Wagner, F., Blaszczyk, R., Kosaric, N. (1993) Biosurfactants for environmental control, in: Biosurfactants: Production, Properties, Applications ( N. Kosaric, Ed.), Marcel Dekker, New York, 447–469.
- Mulligan, C. N., Gibbs, B. F. (1990) Recovery of biosurfactants by ultrafiltration, J. Chem. Tech. Biotechnol. 47, 23–29.
- Mulligan, C. N., Gibbs, B. F. (1993) Factors influencing the economics of biosurfactants, in: Biosurfactants, Production, Properties, Applications ( N. Kosaric, Ed.), Marcel Dekker, New York, 329–371.
- Mulligan, C. N., Yong, R. N., Gibbs, B. F. (1999) On the use of biosurfactants for the removal of heavy metals from oil contaminated soil, Process Safety Prog. 18, 50–54.
- Mutua, L. N., Akoh, C. C. (1993) Lipase catalyzed modification of phospholipids, incorporation of n-3-fatty acids into biosurfactants, J. Am. Oil Chem. Soc. 70, 125–128.
- Oberbremer, A., Muller-Hurtig, R., Wagner, F. (1990) Effect of the addition of microbial surfactant on hydrocarbon degradation in a soil population in a stirred reactor, Appl. Microbiol. Biotechnol. 32, 485–489.
- Ochsner, U. A., Reiser, J. (1995) . Autoinducer-mediated regulation of rhamnolipid biosurfactant synthesis in Pseudomonas aeruginosa, Proc. Natl Acad. Sci. USA 92, 6424–6428.
- Ochsner, U. A., Fiechter, A., Reiser, J. (1994a) . Isolation, characterization and expression in Escherichia coli of the Pseudomonas aeruginosa rhlAB genes encoding a rhamnosyltransferase involved in rhamnolipid biosurfactant synthesis, J. Biol. Chem. 269, 19787–19795.
- Ochsner, U. A., Koch, A. K., Fiechter, A., Reiser, J. (1994b) Isolation and characterization of a regulatory gene affecting rhamnolipid biosurfactant synthesis in Pseudomonas aeruginosa, J. Bacteriol. 176, 2044–2054.
- Ochsner, U. A., Hembach, T., Fiechter, A. (1995a) Production of rhamnolipid biosurfactants, Adv. Biochem. Eng. Biotechnol. 53, 89–118.
- Ochsner, U. A., Reiser, J., Fiechter, A., Witholt, B. (1995b) . Production of Pseudomonas aeruginosa rhamnolipid biosurfactants in heterogeneous host, Appl. Environ. Microbiol. 61, 3503–3506.
- Ozeki, Y., Kaneda, K., Fujiwara, N., Morimoto, M., Oka, S., Yano, I. (1997) In vivo induction of apoptosis in the thymus by administration of Mycobacterial cord factor (trehalose-6,6′-dimycolate), Infect. Immun. 65, 1793–1799.
- Palejwala, S., Desai, J. D. (1989) Production of extracellular emusifier by a Gram negative bacterium, Biotechnol. Lett. 11, 115–118.
- Patel, R. M., Desai, A. J. (1997) Biosurfactant production by Pseudomonas aeruginosa GS3 from molasses, Lett. Appl. Microbiol. 25, 91–94.
- Poremba, K., Lang, S., Wagner, F, Gunkel, W. (1991) Marine biosurfactants. III. Toxicity testing with marine microorganisms and comparison with synthetic surfactants, Z. Naturforsch. 46c, 210–216.
- Powalla, M., Lang, S., Wray, V. (1989) Penta- and disaccharide lipid formation by Nocardia corynebacteroides grown on n-alkanes, Appl. Microbiol. Biotechnol. 31, 473–479.
- Providenti, M. A., Flemming, C. A., Lee, H., Trevors, J. T. (1995) Effect of addition of rhamnolipid biosurfactants or rhamnolipid-producing Pseudomonas aeruginosa on phenanthrene mineralization in soil slurries, FEMS Microbiol. Ecol. 17, 15–26.
- Ragheb, A. T., Al-Tahhan Sandrin, T. R., Bodour, A. A., Maier, R. M. (2000) Rhamnolipid induced removal of lipopolysaccharide from Pseudomonas aeruginosa: effect in cell surface properties and interaction with hydrophobic substrates, Appl. Environ. Microbiol. 66, 3262–3268.
- Rapp, P., Bock, H., Wray, V., Wagner, F. (1979) Formation, isolation and characterization of trehalose dimycolates from Rhodococcus erythropolis grown on n-alkanes, J. Gen. Microbiol. 115, 491–503.
- Reiling, H. E., Wyass, U. T., Guerra-Santos, L. H., Hirt, R., Kappali, O., Fiechter, A. (1986) Pilot plant production of rhamnolipid biosurfactant by Pseudomonas aeruginosa, Appl. Environ. Microbiol. 51, 985–989.
- Reisch, M. C. (2000) Hair care products, Chem. Eng. News 78 (12), 15–26.
- Ristau, E., Wagner, F. (1993) Formation of novel anionic trehalose-tetraesters from Rhodococcus erythropolis under growth limiting conditions, Biotechnol. Lett. 5, 95–100.
- Robert, M., Mercade, M. E., Bosch, M. P., Parra, J. L., Espuny, M. J., Manresa, M. A., Guinea, J. (1989) Effect of the carbon source on biosurfactant production by Pseudomonas aeruginosa 44T, Biotechnol. Lett. 11, 871–874.
- Roger, P., de Bentzmann, S. (1998) Pseudomonas aeruginosa adherence to the respiratory mucosa, Medicine Maladies Infect. 28, 119–125.
- Rosenberg, E. (1993) Exploiting microbial growth on hydrocarbon – new markets, Trends Biotechnol. 11, 419–424.
- Rosenberg, E., Zuckerberg, A., Rubinovitz, C., Gutnick, D. L. (1979) Emulsifier Arthrobacter RAG-1, isolation and emulsifying properties, Appl. Environ. Microbiol. 37, 402–408.
- Rosenberg, E., Rubinovitz, C., Gottlieb, A., Rosenhak, S., Ron, E. Z. (1988a) Production of biodispersan by Acinetobacter calcoaceticus A2, Appl. Environ. Microbiol. 54, 317–322.
- Rosenberg, E., Rubinovitz, C., Legmann, R., Ron, E. Z. (1988b) Purification and chemical properties of Acinetobacter calcoaceticus A2 biodispersan, Appl. Environ. Microbiol. 54, 323–326.
- Sandrin, T. R., Chech, A. M., Maier, R. M. (2000) A rahmnolipd biosurfactant reduces cadmium toxicity during naphthalene biodegradation, Appl. Environ. Microbiol. 66, 4585–4588.
- Sarney, D. B., Vulfson, E. N. (1995) Application of enzymes to the synthesis of surfactants, Trends Biotechnol. 13, 164–175.
- Scheckermann, C., Schlotterbeck, A., Schmidt, M., Wray, V., Lang, S. (1995) Enzymatic monoacylation of fructose by two procedures, Enz. Microbial. Technol. 17, 157–162.
- Scheibenbogen, K., Zytner, R. G., Lee, H., Trevors, J. T. (1994) Enhanced removal of selected hydrocarbons from soil by Pseudomonas aeruginosa UG2 biosurfactants and some chemical surfactants, J. Chem. Technol. Biotechnol. 59, 53–59.
- Sharve, G. S., Ingura, S., Gunnam, C. (1995) Rhamnolipid biosurfactant enhancement of hexadecane biodegradation by Pseudomonas aeruginosa, Mol. Mar. Biol. Biotechnol. 4, 331–337
- Sieman, M., Wagner, F. (1993) Prospects and limits for the production of biosurfactants using immobilized biocatalysts, in: Biosurfactants, Production, Properties, Applications ( N. Kosaric, Ed.), Marcel Dekker, New York, 99–133.
- Sigmond, I., Wagner, F. (1991) New Method for detecting rhamnolipids excreted by Pseudomonas species grown on mineral agar, Biotechnol. Tech. 5, 265–268.
- Stanghellini, M. E., Miller, R. M. (1997) Biosurfactants – their identity and potential efficacy in the biological control of Zoosporic plant pathogens, Plant Dis. 81, 4–12
- Suzuki, T., Tanaka, H., Itoh, S. (1974) Sucrose lipids of Arthrobacteria, Corynebacteria and Nocardia grown on sucrose, Agric. Biol. Chem. 38, 557–563.
- Suzuki, T., Tanaka, K., Matsubara, I., Kinoshita, S. (1969) Trehalose lipids and alpha branched beta hydroxyfatty acids formed by bacteria grown on n-alkanes, Agric. Biol. Chem. 33, 1619–1627.
- Syldatk, C., Lang, S., Wagner, F. (1985) Chemical and physical characterization of four interfacial-active rhamnolipids from Pseudomonas sp. DSM 2874 grown on n-alkanes, Z. Naturforsch. 40c, 51–60.
- Torres, C., Bernabe, M., Otero, C. (2000) . Enzymatic synthesis of lactic acid derivatives with emulsifying properties, Biotechnol. Lett. 22, 331–334.
- Totani, Y., Hara, S. (1991) Preparation of polyunsaturated phospholipids by lipase-catalysed transesterification, J. Am. Oil Chem. Soc. 68, 848–851.
- Uchida, Y., Tsuchiya, R., Chino, M., Hirano, J., Tabuchi, T. (1989) Extracellular accumulation of mono- and di-succinyl trehalose lipids by a strain of Rhodococcus erythropolis grown on n-alkanes, Agric. Biol. Chem. 53, 757–763.
- Van der Vegt, W., Vander Mei, H. C., Noordmans, J., Busscher, H. J. (1991) Assessment of bacterial biosurfactant production through axisymmetric drop shape analysis by profile, Appl. Microbiol. Biotechnol. 35, 766–770.
- Van Dyke, M. I., Counture, P., Brauer, M., Lee, H., Trevors, J. T. (1993) Pseudomonas aeruginosa UG2 rhamnolipid biosurfactants: structural characterization and their use in removing hydrophobic compounds from soil, Can. J. Microbiol. 39, 1071–1078.
- Vollbrecht, E., Heckmann, R., Wray, V., Nimtz, M., Lang, S. (1998) Production and structure elucidation of di- and oligosaccharide lipids (biosurfactants) from Tsukamurella sp. Nov, Appl. Microbiol. Biotechnol. 50, 530–537.
-
Vollbrecht, E.,
Rau, U.,
Lang, S.
(1999)
Microbial conversion of vegetable oils into surface active di-, tri-, and tetrasaccharide lipids (biosurfactants) by the bacterial strain Tsukamurella sp.,
Fats Lipids 101,
389–394.
10.1002/(SICI)1521-4133(199910)101:10<389::AID-LIPI389>3.0.CO;2-9 CAS Web of Science® Google Scholar
- Wicke, C., Huners, M., Wray, V., Nimtz, M., Bilitewsky, U., Lang, S. (2000) Production and structure elucidation of glycoglycerolipids from marine sponge associated Microbacterium sp., J. Nat. Prod. 63, 621–626.
- Yakimov, N. M., Golyshin, P. N., Lang, S., Moore, E. R. B., Abraham, W. R., Lunsdorf, H., Timmis, K. N. (1998) Alcanivorax borkumensis gen. nov., Sp. nov., a new, hydrocarbon degrading and surfactant producing marine bacterium, Int. J. Syst. Bacteriol. 48, 339–348.
- Yamaguchi, M., Sato, A., Yukuyama, A. (1976) Microbial production of sugar lipids, Chem. Ind. 17, 741–742.
- Zhang, Y., Miller, R. M. (1994) Effect of a Pseudomonas rhamnolipid biosurfactant on cell hydrophobicity and biodegradation of octadecane, Appl. Environ. Microbiol. 60, 2101–2106.
- Zhang, Y., Miller, R. M. (1995) Effect of rhamnolipid (biosurfactant) structure on solubilization and biodegradation of n-alkanes, Appl. Environ. Microbiol. 61, 2247–2251.
Biopolymers Online: Biology • Chemistry • Biotechnology • Applications
Browse other articles of this reference work: