Abstract
5'-Aziridinoadenylates of the form 1 and a related nitrogen mustard variant have been constructed using a novel variation of the Mitsunobu reaction. Such molecules allow conversion of biological methyltransferases into nucleoside transferases, thus providing powerful tools for investigating S-adenosyl-l-methionine (SAM)-dependent methylation. We present here a highly effective synthesis of such molecules that is amenable to aziridine diversification as well as elaboration of the base moiety so as to afford "bumped" cofactor mimics compatible with "hole"-bearing mutant proteins.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Adenosine / analogs & derivatives
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Adenosine / chemical synthesis*
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Aziridines / chemical synthesis*
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DNA Nucleotidylexotransferase / metabolism
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Methylation
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Methyltransferases / metabolism
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Molecular Mimicry
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Mustard Plant / metabolism
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Nitrobenzenes / chemistry*
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Nucleosides / chemical synthesis*
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S-Adenosylmethionine / chemistry
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S-Adenosylmethionine / metabolism
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Spectrum Analysis
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Sulfonamides / chemistry
Substances
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Aziridines
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Nitrobenzenes
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Nucleosides
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Sulfonamides
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S-Adenosylmethionine
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Methyltransferases
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DNA Nucleotidylexotransferase
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Adenosine