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Predicate | Object |
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rdf:type | |
lifeskim:mentions | |
pubmed:issue |
14
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pubmed:dateCreated |
1995-9-1
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pubmed:abstractText |
The synthesis of a new class of multisubstrate adduct inhibitors of polyamine biosynthesis has been investigated. The first target compound, designed to inhibit spermidine synthase, was obtained and proved to be a very potent inhibitor of that enzyme. Two synthetic routes to effect the coupling of the polyamine spermidine to the nucleoside adenosine were studied. The first route involved a proposed Wittig or Julia olefination reaction to form the critical 5'-6' carbon-carbon bond between the nucleoside and polyamine moieties. This route failed due to a facile beta-elimination of a portion of the side chain from a carbanion intermediate during either coupling reaction. A second route involved a reductive amination approach and proved to be successful. The new inhibitor, given the trivial name adenosylspermidine, is the most potent inhibitor of spermidine synthase prepared to date.
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pubmed:grant | |
pubmed:language |
eng
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pubmed:journal | |
pubmed:citationSubset |
IM
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pubmed:chemical | |
pubmed:status |
MEDLINE
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pubmed:month |
Jul
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pubmed:issn |
0022-2623
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pubmed:author | |
pubmed:issnType |
Print
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pubmed:day |
7
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pubmed:volume |
38
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pubmed:owner |
NLM
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pubmed:authorsComplete |
Y
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pubmed:pagination |
2714-27
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pubmed:dateRevised |
2007-11-14
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pubmed:meshHeading |
pubmed-meshheading:7629810-Adenosine,
pubmed-meshheading:7629810-Animals,
pubmed-meshheading:7629810-CHO Cells,
pubmed-meshheading:7629810-Cell Line,
pubmed-meshheading:7629810-Cricetinae,
pubmed-meshheading:7629810-Haplorhini,
pubmed-meshheading:7629810-Humans,
pubmed-meshheading:7629810-Magnetic Resonance Spectroscopy,
pubmed-meshheading:7629810-Spermidine,
pubmed-meshheading:7629810-Spermidine Synthase,
pubmed-meshheading:7629810-Tumor Cells, Cultured
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pubmed:year |
1995
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pubmed:articleTitle |
Synthesis and biochemical evaluation of adenosylspermidine, a nucleoside-polyamine adduct inhibitor of spermidine synthase.
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pubmed:affiliation |
Department of Chemistry, University of Michigan, Ann Arbor 48109-1055, USA.
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pubmed:publicationType |
Journal Article,
Research Support, U.S. Gov't, P.H.S.
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