2'-deoxy-1-methylpseudocytidine, a stable analog of 2'-deoxy-5-methylisocytidine.

Abstract

2'-deoxy-5-methylisocytidine is widely used in assays to personalize the care of patients infected with HIV, hepatitis C, and other infectious agents. However, oligonucleotides that incorporate 2'-deoxy-5-methylisocytidine are expensive, because of its intrinsic chemical instability. We report here a C-glycoside analog that is more stable and, in oligonucleotides, pairs with 2'-deoxyisoguanosine, contributing to duplex stability about as much as a standard 2'-deoxycytidine and 2'-deoxyguanosine pair.

• Authors: Hyo-Joong Kim, Nicole A Leal, Steven A Benner
• Journal: Bioorganic & medicinal chemistry (Bioorg Med Chem) Vol. 17 Issue 10 Pg. 3728-32 (May 15 2009) ISSN: 1464-3391 [Electronic] England
• PMID: 19394831 (Publication Type: Journal Article, Research Support, N.I.H., Extramural, Research Support, Non-U.S. Gov't)

Chemical References

• 2'-deoxy-1-methylpseudocytidine
• 2'-deoxy-5-methylisocytidine
• Oligodeoxyribonucleotides
• Cytidine

Topics

• Base Pairing
• Base Sequence
• Chromatography, High Pressure Liquid
• Cytidine (analogs & derivatives, chemical synthesis, chemistry)
• Oligodeoxyribonucleotides (chemical synthesis, chemistry)
• Transition Temperature