Communication

Bifacial Nucleoside as a Surrogate for Both T and A in Duplex DNA

Dongwon Shin and Yitzhak Tor*
Department of Chemistry and Biochemistry, University of California, San Diego, La Jolla, California 92093-0358, United States
J. Am. Chem. Soc., 2011, 133 (18), pp 6926–6929
DOI: 10.1021/ja201397e
Publication Date (Web): April 15, 2011
Copyright © 2011 American Chemical Society

Abstract

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A new functional bifacial nucleoside derived from 7-aminopyrimido[4,5-d]pyrimidine-2,4(1H,3H)-dione, a Janus-type nucleobase, has been synthesized and incorporated into DNA oligonucleotides. The nucleobase, having self-complementary H-bonding faces, mimics both T and A and engages in the corresponding Watson–Crick-like base pairs, forming stable duplexes.

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History

  • Published In Issue May 11, 2011
  • Article ASAPApril 15, 2011
  • Received: February 14, 2011

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