Bunji Shimizu

Optical rotatory dispersion of the anomeric nucleosides and nucleotides

Abstract 1. 1. Optical rotatory dispersion data for about 40 anomeric nucleosides and their 5′-phosphates are presented. 2. 2. The compounds include nucleosides and nucleotides of d - and l -ribofuranose, d - and l -arabinofuranose, d - and l -lyxofuranose and l -xylofuranose. 3. 3. β- d - and α- l -pentofuranosylpyrimidines give single positive Cotton effects whereas α- d - and β- l -derivatives, negative effects. 4. 4. Configuration at the anomeric carbon determines the sign of the Cotton effect and that at C-2′ profoundly affects the amplitude. However, configurations at C-3′ and C-4′ influence neither the sign nor the amplitude of the Cotton effects. 5. 5. α- d -Adenosine and α- d -AMP exhibit positive Cotton effects, while β- d -adenosine and β- d -AMP, negative. 6. 6. 3-β- d - and 3-β- l -ribofuranosyladenine 5′-phosphate (β- l -IsoAMP) and 7-α- d - and 7-β- d -ribofuranosyltheophylline give multiple Cotton effects in ultraviolet region. β- d -IsoAMP exhibits a negative effect centered at its ultraviolet absorption maximum, while the sign of the first Cotton effect of 7-β- d -ribofuranosyltheophylline is positive.