Syntheses of pyridine C-nucleosides as analogues of the natural nucleosides dC and dU.
The syntheses of four pyrimidine C-nucleosides are described. These derivatives are designed as mimics of dC and dU, and in that respect, each can form two hydrogen bonds with complementary dG or dA residues. The minor groove O2 carbonyl in each derivative is replaced by a fluorine or a methyl group. The key carbon-carbon bond connecting the heterocycle to the carbohydrate is formed using a Heck-type palladium-mediated coupling reaction.
Sun
Zhenhua
Z
Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, MA 02467, USA.
Ahmed
Shahadat
S
McLaughlin
Larry W
LW
D003841:Deoxycytidine / Q000737:chemistry*; D003857:Deoxyuridine / Q000737:chemistry*; D006860:Hydrogen Bonding; D009690:Nucleic Acid Conformation; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D011725:Pyridines / Q000737:chemistry*; D013237:Stereoisomerism
D009705:Nucleosides; D011725:Pyridines; D003841:Deoxycytidine; D003857:Deoxyuridine