Novel method for the synthesis of N4-methyl and hydroxy cytidine phosphoramidites

ORGN 394

Jun Lu, jlu@uchicago.edu, Nan-Sheng Li, nli@uchicago.edu, and Joseph A. Piccirilli, jpicciri@uchicago.edu. Departments of Biochemistry & Molecular Biology and Chemistry, Howard Hughes Medical Institute, University of Chicago, 929 East 57th Street, Room W406, Chicago, IL 60637

N4-Methyl and N4-hydroxylamino modified cytosine analogues have been incorporated into oligonucleotides and are being used to investigate catalysis by the hepatitis delta virus ribozyme. The N4-hydroxylamino modification can be used to determine whether a tautomeric form of cytosine with a protonated N3 is functionally relevant. Two new modified cytidine

phosphoramidites were synthesized starting from uridine in 40.7 and 26.8% yield, respectively, for this study.

 

New Reactions and Methodology, Total Synthesis, Materials, Devices and Switches, Lipids, Nucleotides and Mimetics
8:00 PM-10:00 PM, Tuesday, March 27, 2007 Hyatt Regency Chicago -- Riverside Center, Poster

Division of Organic Chemistry

The 233rd ACS National Meeting, Chicago, IL, March 25-29, 2007