Carbon isotope-labelling experiments indicate that ladderane lipids of anammox bacteria are synthesized by a previously undescribed, novel pathway Export

@article{citeulike:5400617, abstract = {Ladderane lipids are unusual membrane lipids of bacteria that anaerobically oxidize ammonium to dinitrogen gas (anammox). Ladderane lipids contain linearly concatenated cyclobutane rings for which the pathway of biosynthesis is currently unknown. To investigate the possible biosynthetic routes of these lipids, 2-13C-labelled acetate was added to a culture of the anammox bacterium Candidatus Brocadia fulgida. Labelling patterns obtained by high-field 13C nuclear magnetic resonance spectroscopy of isolated lipids indicated that C. Brocadia fulgida synthesizes C16:0 and isoC16:0 fatty acids according to the known pathway of type II fatty acid biosynthesis. The 13C-labelling pattern of the C8 alkyl chain of the C20 [3] ladderane monoether also indicated the use of this route. However, carbon atoms in the cyclobutane rings and the cyclohexane ring were nonspecifically labelled and did not correspond to known patterns of fatty acid synthesis. Taken together, our results indicate that it is unlikely that ladderane lipids are formed from the cyclization of polyunsaturated fatty acids as hypothesized previously and suggest an alternative, although as yet unknown, pathway of biosynthesis.}, address = {Department of Marine Organic Biogeochemistry, NIOZ Royal Netherlands Institute for Sea Research, Texel, The Netherlands; NMR Department, van't Hoff Institute for Molecular Sciences, University of Amsterdam, Amsterdam, The Netherlands; and; Department of Microbiology, Radboud University Nijmegen, Toernooiveld, Nijmegen, The Netherlands}, author = {Rattray, Jayne E. and Geenevasen, Jan A. J. and van Niftrik, Laura and Irene and Hopmans, Ellen C. and Strous, Marc and Schouten, Stefan and Jetten, Mike S. M. and Sinninghe Damst\'{e}, Jaap S.}, citeulike-article-id = {5400617}, citeulike-linkout-0 = {http://dx.doi.org/10.1111/j.1574-6968.2008.01483.x}, citeulike-linkout-1 = {http://www3.interscience.wiley.com/cgi-bin/abstract/121645182/ABSTRACT}, doi = {10.1111/j.1574-6968.2008.01483.x}, issn = {1574-6968}, journal = {FEMS Microbiology Letters}, keywords = {anammox, ladderane, lipids, physiology}, number = {1}, pages = {115--122}, posted-at = {2009-08-09 11:46:12}, priority = {0}, title = {Carbon isotope-labelling experiments indicate that ladderane lipids of anammox bacteria are synthesized by a previously undescribed, novel pathway}, url = {http://dx.doi.org/10.1111/j.1574-6968.2008.01483.x}, volume = {292}, year = {2009} }

TY - JOUR ID - citeulike:5400617 L3 - citeulike-article-id:5400617 N2 - Ladderane lipids are unusual membrane lipids of bacteria that anaerobically oxidize ammonium to dinitrogen gas (anammox). Ladderane lipids contain linearly concatenated cyclobutane rings for which the pathway of biosynthesis is currently unknown. To investigate the possible biosynthetic routes of these lipids, 2-13C-labelled acetate was added to a culture of the anammox bacterium Candidatus Brocadia fulgida. Labelling patterns obtained by high-field 13C nuclear magnetic resonance spectroscopy of isolated lipids indicated that C. Brocadia fulgida synthesizes C16:0 and isoC16:0 fatty acids according to the known pathway of type II fatty acid biosynthesis. The 13C-labelling pattern of the C8 alkyl chain of the C20 [3] ladderane monoether also indicated the use of this route. However, carbon atoms in the cyclobutane rings and the cyclohexane ring were nonspecifically labelled and did not correspond to known patterns of fatty acid synthesis. Taken together, our results indicate that it is unlikely that ladderane lipids are formed from the cyclization of polyunsaturated fatty acids as hypothesized previously and suggest an alternative, although as yet unknown, pathway of biosynthesis. IS - 1 JF - FEMS Microbiology Letters SN - 1574-6968 AD - Department of Marine Organic Biogeochemistry, NIOZ Royal Netherlands Institute for Sea Research, Texel, The Netherlands; NMR Department, van't Hoff Institute for Molecular Sciences, University of Amsterdam, Amsterdam, The Netherlands; and; Department of Microbiology, Radboud University Nijmegen, Toernooiveld, Nijmegen, The Netherlands EP - 122 TI - Carbon isotope-labelling experiments indicate that ladderane lipids of anammox bacteria are synthesized by a previously undescribed, novel pathway VL - 292 SP - 115 KW - anammox KW - ladderane KW - lipids KW - physiology AU - Rattray, Jayne AU - Geenevasen, Jan AU - van Niftrik, Laura AU - Irene AU - Hopmans, Ellen AU - Strous, Marc AU - Schouten, Stefan AU - Jetten, Mike AU - Sinninghe Damsté, Jaap PY - 2009/// UR - http://dx.doi.org/10.1111/j.1574-6968.2008.01483.x ER -