Efficient synthesis of azide-bearing cofactor mimics.

Lindsay R Comstock, Scott R Rajski

University of Wisconsin-Madison, School of Pharmacy, 777 Highland Avenue, Madison, Wisconsin 53705, USA.

The Journal of organic chemistry 2004 Feb 20

filter terms:

8-Azido-5'-aziridino-5'-deoxyadenosine (6), a novel cofactor mimic, was synthesized in nine steps from commercially available 2',3'-isopropylideneadenosine in approximately 4% overall yield. Crucial to this success was a very unorthodox phthalimide cleavage procedure, C8 azidation prior to aziridination and late stage alkylation of the 5' amino group with iodoethanol necessitated by the high degree of lability endowed by the aryl azide moiety. Aziridine 6 is envisioned as a useful biochemical tool by which to probe DNA and protein methylation patterns.

Citation

Lindsay R Comstock, Scott R Rajski. Efficient synthesis of azide-bearing cofactor mimics. The Journal of organic chemistry. 2004 Feb 20;69(4):1425-8