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-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.
Petersen
Scott G
SG
The School of Pharmacy and Department of Chemistry, University of Wisconsin-Madison, 777 Highland Avenue, Madison, WI 53705-2222, USA.
Rajski
Scott R
SR
D000241:Adenosine / Q000031:analogs & derivatives / Q000138:chemical synthesis*; D001388:Aziridines / Q000138:chemical synthesis*; D004253:DNA Nucleotidylexotransferase / Q000378:metabolism; D008745:Methylation; D008780:Methyltransferases / Q000378:metabolism; D018716:Molecular Mimicry; D009149:Mustard Plant / Q000378:metabolism; D009578:Nitrobenzenes / Q000737:chemistry*; D009705:Nucleosides / Q000138:chemical synthesis*; D012436:S-Adenosylmethionine / Q000737:chemistry / Q000378:metabolism; D013057:Spectrum Analysis; D013449:Sulfonamides / Q000737:chemistry
D001388:Aziridines; D009578:Nitrobenzenes; D009705:Nucleosides; D013449:Sulfonamides; D012436:S-Adenosylmethionine; D008780:Methyltransferases; D004253:DNA Nucleotidylexotransferase; D000241:Adenosine