Journal
TETRAHEDRON
Volume 58, Issue 30, Pages 6019-6026Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0040-4020(02)00590-2
Keywords
S-adenosyl-L-methionine; aziridine-based cofactor mimics; 5 '-aminoadenosine; Gabriel-Cromwell
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S-Adenosyl-L-methionine mimics were synthesized in a linear fashion highlighting methodology that bypasses the need for adenine base protection. These aziridine-based cofactor mimics are envisioned as useful biochemical tools and potential therapeutic agents whose mechanism of action hinges upon aberrant methyltransferase enzymes. Aziridination of the 5' position of adenosine was effected by convergence of suitably protected 5'-aminoadenosine with various dibromopropionates. The economy and high yields for this route to said aziridine-based cofactors is highly amenable to large-scale chemistry which no doubt will be vital to their development as therapeutics and biochemical tools. (C) 2002 Elsevier Science Ltd. All rights reserved.
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