o-Nitrobenzenesulfonamides in Nucleoside Synthesis:  Efficient 5‘-Aziridination of Adenosine

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-adenos...

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Veröffentlicht in:Journal of organic chemistry 2005-07, Vol.70 (15), p.5833-5839
Hauptverfasser: Petersen, Scott G, Rajski, Scott R
Format: Artikel
Sprache:eng
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Zusammenfassung: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo050205w