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Department of Materials Science and Engineering, University of Illinois at Urbana – Champaign, 1304 West Green Street, Urbana, USA
; Fax: +1-217-333-2736
; Tel: +1-217-244-3924.
Chem. Sci., 2012,3, 2234-2239
25 Feb 2012,
06 Apr 2012
First published online
11 Apr 2012
Several Zn β-diiminate reagents were developed and used to mediate regioselective O-acylation reactions of therapeutic agents with anhydrides. Various prodrugs were obtained in excellent yield and high regioselectivity, including derivatives of rapamycin and paclitaxel. Furthermore, the application of regioselective acylation was extended to one-pot reactions between therapeutics and carboxylic acids with various pendant functional groups. This rapid functionalization strategy will find application in either prodrug synthesis or bioconjugation for drug delivery.
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