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...
Gespeichert in:
Veröffentlicht in: | Journal of organic chemistry 2005-07, Vol.70 (15), p.5833-5839 |
---|---|
Hauptverfasser: | , |
Format: | Artikel |
Sprache: | eng |
Schlagworte: | |
Online-Zugang: | Volltext |
Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
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 |