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Predicate | Object |
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rdf:type | |
lifeskim:mentions | |
pubmed:issue |
2
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pubmed:dateCreated |
1997-2-12
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pubmed:abstractText |
The biosynthesis of the pancreatic lipase inhibitor lipstatin was investigated by fermentation experiments using cultures of Streptomyces toxytricini, which were supplied with soybean oil and a crude mixture of U-13C-lipids obtained from algal biomass cultured with 13CO2. Lipstatin was analyzed by one- and two-dimensional NMR spectroscopy. 13C total correlation spectroscopy and INADEQUATE experiments show that two fatty acid fragments containing 14 and 8 carbon atoms, respectively, are incorporated en bloc into lipstatin. The 14-carbon fragment is preferentially derived from the unsaturated fatty acid fraction, as shown by an experiment with hydrogenated U-13C-lipid mixture, which is conducive to labeling of the 8-carbon moiety but not of the 14-carbon moiety. The data indicate that the lipstatin molecule can be assembled by Claisen condensation of octanoyl-CoA with 3-hydroxy-delta5,8-tetradecanoyl-CoA obtained by beta oxidation of linoleic acid. The formation of lipstatin from acetate units by a polyketide-type pathway is ruled out conclusively by these data. The data show that surprisingly clear labeling patterns can be obtained in studies with crude, universally 13C-labeled precursor mixtures that are proffered together with a large excess of unlabeled material. One- and two-dimensional 13C total correlation spectroscopy analyses are suggested as elegant methods for the delineation of contiguously 13C-labeled biosynthetic blocks.
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pubmed:language |
eng
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pubmed:journal | |
pubmed:citationSubset |
IM
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pubmed:chemical |
http://linkedlifedata.com/resource/pubmed/chemical/Enzyme Inhibitors,
http://linkedlifedata.com/resource/pubmed/chemical/Lactones,
http://linkedlifedata.com/resource/pubmed/chemical/Lipase,
http://linkedlifedata.com/resource/pubmed/chemical/lipstatin,
http://linkedlifedata.com/resource/pubmed/chemical/orlistat
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pubmed:status |
MEDLINE
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pubmed:month |
Jan
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pubmed:issn |
0021-9258
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pubmed:author | |
pubmed:issnType |
Print
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pubmed:day |
10
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pubmed:volume |
272
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pubmed:owner |
NLM
|
pubmed:authorsComplete |
Y
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pubmed:pagination |
867-74
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pubmed:dateRevised |
2006-11-15
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pubmed:meshHeading | |
pubmed:year |
1997
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pubmed:articleTitle |
Tracer studies with crude U-13C-lipid mixtures. Biosynthesis of the lipase inhibitor lipstatin.
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pubmed:affiliation |
Department of Organic Chemistry and Biochemistry, Technical University of Munich, Federal Republic of Germany.
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pubmed:publicationType |
Journal Article,
Research Support, Non-U.S. Gov't
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