Positional specificity of cyclopropane ring formation from cis-octadecenoic acid isomers in Escherichia coli
dc.contributor.author | Ohlrogge, John B. | en_US |
dc.contributor.author | Gunstone, Frank D. | en_US |
dc.contributor.author | Ismail, I. A. | en_US |
dc.contributor.author | Lands, William E. M. | en_US |
dc.date.accessioned | 2006-04-07T16:28:39Z | |
dc.date.available | 2006-04-07T16:28:39Z | |
dc.date.issued | 1976-05-27 | en_US |
dc.identifier.citation | Ohlrogge, John B., Gunstone, Frank D., Ismail, I. A., Lands, William E. M. (1976/05/27)."Positional specificity of cyclopropane ring formation from cis-octadecenoic acid isomers in Escherichia coli." Biochimica et Biophysica Acta (BBA) - Lipids and Lipid Metabolism 431(2): 257-267. <http://hdl.handle.net/2027.42/21769> | en_US |
dc.identifier.uri | http://www.sciencedirect.com/science/article/B6T1X-47G2RRH-7P/2/7f5493a7dd49bb27d4286d9ea1906691 | en_US |
dc.identifier.uri | https://hdl.handle.net/2027.42/21769 | |
dc.identifier.uri | http://www.ncbi.nlm.nih.gov/sites/entrez?cmd=retrieve&db=pubmed&list_uids=779836&dopt=citation | en_US |
dc.description.abstract | An unsaturated fatty acid auxotroph of Escherichia coli was grown with a series of cis-octadecenoate isomers in which the location of the double bond varied from positions 3 to 17. Each of these fatty acid isomers was incorporated into the cellular lipids, but cyclopropane derivatives were formed to at least a 3-fold greater extent from the cis-9 and cis-11 isomers than from any other positional isomers. The extent of cyclopropane acid formation was observed to be highly dependent on the rate of shaking of the culture. A culture shaking at 340 rev./min converted 8.7% of its oleate to the cyclopropane derivative at stationary phase, whereas a parellel culture shaken at 110 rev./min converted 66% of the oleate to a cyclopropane acid.The inability to observe selectivity or form derivatives from isomers other than the is-9 and cis-11 isomers seems to be due to enzyme specificity rather than a secondary affect of the abnormal unconverted fatty acids on the cell, because the cis-9 isomer is converted to its cyclopropane derivative even in cells grown with abnormal unreactive positional isomers.The preferred substrates for cyclopropanecarboxylic acid formation contained a cis ethylenic bond at either the 9 position or the -7 position. In combination with results of previous studies the specificity reported here supports a concept that two different enzymes may participate in cyclopropane ring synthesis. One enzyme activity may recognize its substrate by the distance from the [pi]-bond to the carboxyl group and the other by the distance to the methyl group. | en_US |
dc.format.extent | 832024 bytes | |
dc.format.extent | 3118 bytes | |
dc.format.mimetype | application/pdf | |
dc.format.mimetype | text/plain | |
dc.language.iso | en_US | |
dc.publisher | Elsevier | en_US |
dc.title | Positional specificity of cyclopropane ring formation from cis-octadecenoic acid isomers in Escherichia coli | en_US |
dc.type | Article | en_US |
dc.rights.robots | IndexNoFollow | en_US |
dc.subject.hlbsecondlevel | Materials Science and Engineering | en_US |
dc.subject.hlbsecondlevel | Chemistry | en_US |
dc.subject.hlbsecondlevel | Chemical Engineering | en_US |
dc.subject.hlbtoplevel | Science | en_US |
dc.subject.hlbtoplevel | Engineering | en_US |
dc.description.peerreviewed | Peer Reviewed | en_US |
dc.contributor.affiliationum | The Department of Biological Chemistry, The University of Michigan, Ann Arbor, Mich. 48104, U.S.A.: Department of Chemistry, St. Andrews University, St. Andrews, U.K. | en_US |
dc.contributor.affiliationum | The Department of Biological Chemistry, The University of Michigan, Ann Arbor, Mich. 48104, U.S.A.: Department of Chemistry, St. Andrews University, St. Andrews, U.K. | en_US |
dc.contributor.affiliationum | The Department of Biological Chemistry, The University of Michigan, Ann Arbor, Mich. 48104, U.S.A.: Department of Chemistry, St. Andrews University, St. Andrews, U.K. | en_US |
dc.contributor.affiliationum | The Department of Biological Chemistry, The University of Michigan, Ann Arbor, Mich. 48104, U.S.A.: Department of Chemistry, St. Andrews University, St. Andrews, U.K. | en_US |
dc.identifier.pmid | 779836 | en_US |
dc.description.bitstreamurl | http://deepblue.lib.umich.edu/bitstream/2027.42/21769/1/0000163.pdf | en_US |
dc.identifier.doi | http://dx.doi.org/10.1016/0005-2760(76)90146-6 | en_US |
dc.identifier.source | Biochimica et Biophysica Acta | en_US |
dc.owningcollname | Interdisciplinary and Peer-Reviewed |
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