title: A highly facile and efficient one-step synthesis of N6-adenosine and N6-2'-deoxyadenosine derivatives.
abstract: [reaction: see text] A highly facile and efficient one-step synthesis of N6-adenosine and N6-2'-deoxyadenosine derivatives has been developed. Treatment of inosine or 2'-deoxyinosine, without protection of sugar hydroxyl groups, with alkyl or arylamines, in the presence of BOP and DIPEA in DMF, led to the formation of N6-adenosine and N6-2'-deoxyadenosine derivatives in good to excellent yields. Carcinogenic polyaromatic hydrocarbon (PAH) N6-2'-deoxyadenosine adduct 10 and a rare DNA constituent 11 were thus synthesized directly from 2'-deoxyinosine both in 98% yield.
authors.affiliation: Chemical and Screening Sciences, Wyeth Research, 200 Cambridge Park Drive, Cambridge, Massachusetts 02140, USA. zwan@wyeth.com
authors.forename: Zhao-Kui
authors.initials: ZK
authors.lastname: Wan
authors.forename: Eva
authors.initials: E
authors.lastname: Binnun
authors.forename: Douglas P
authors.initials: DP
authors.lastname: Wilson
authors.forename: Jinbo
authors.initials: J
authors.lastname: Lee
mesh_terms: D000241:Adenosine / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques; D003839:Deoxyadenosines / Q000138:chemical synthesis*; D015394:Molecular Structure
chemical_list: D003839:Deoxyadenosines; D000241:Adenosine