rdf:type |
|
lifeskim:mentions |
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pubmed:issue |
35
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pubmed:dateCreated |
2008-8-29
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pubmed:abstractText |
This study shows that the role of DNA in the DNA-based enantioselective Diels-Alder reaction of azachalcone with cyclopentadiene is not limited to that of a chiral scaffold. DNA in combination with the copper complex of 4,4'-dimethyl-2,2'-bipyridine (Cu-L1) gives rise to a rate acceleration of up to 2 orders of magnitude compared to Cu-L1 catalysis alone. Furthermore, both the enantioselectivity and the rate enhancement prove to be dependent on the DNA-sequence. These features are the main reasons for the efficient and enantioselective catalysis observed with salmon testes DNA/Cu-L1 in the Diels-Alder reaction. The fact that absolute levels of stereocontrol can be achieved with a simple and weak DNA-binding complex like Cu-L1 is a clear demonstration of the power of the supramolecular approach to hybrid catalysis.
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pubmed:language |
eng
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pubmed:journal |
|
pubmed:citationSubset |
IM
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pubmed:chemical |
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pubmed:status |
MEDLINE
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pubmed:month |
Sep
|
pubmed:issn |
1520-5126
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pubmed:author |
|
pubmed:issnType |
Electronic
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pubmed:day |
3
|
pubmed:volume |
130
|
pubmed:owner |
NLM
|
pubmed:authorsComplete |
Y
|
pubmed:pagination |
11783-90
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pubmed:meshHeading |
pubmed-meshheading:18681429-2,2'-Dipyridyl,
pubmed-meshheading:18681429-Animals,
pubmed-meshheading:18681429-Catalysis,
pubmed-meshheading:18681429-Chalcones,
pubmed-meshheading:18681429-Circular Dichroism,
pubmed-meshheading:18681429-Copper,
pubmed-meshheading:18681429-Cyclopentanes,
pubmed-meshheading:18681429-DNA,
pubmed-meshheading:18681429-DNA, Single-Stranded,
pubmed-meshheading:18681429-Kinetics,
pubmed-meshheading:18681429-Male,
pubmed-meshheading:18681429-Nucleic Acid Conformation,
pubmed-meshheading:18681429-Oligonucleotides,
pubmed-meshheading:18681429-Organometallic Compounds,
pubmed-meshheading:18681429-Salmon,
pubmed-meshheading:18681429-Stereoisomerism,
pubmed-meshheading:18681429-Substrate Specificity
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pubmed:year |
2008
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pubmed:articleTitle |
DNA-based asymmetric catalysis: sequence-dependent rate acceleration and enantioselectivity.
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pubmed:affiliation |
Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen, The Netherlands.
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pubmed:publicationType |
Journal Article,
Research Support, Non-U.S. Gov't
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