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Original Articles

Introduction of 6-Formylcytidine into a Myb Binding Sequence

, , , , , , , , & show all
Pages 2769-2783 | Received 12 Mar 1999, Accepted 01 Jun 1999, Published online: 04 Oct 2006

References

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  • Groziak , M. P. , Koohang , A. , Stevens , W. C. and Robinson , P. D. 1993 . J. Org. Chem. , 58 : 4054 – 4060 . Formyl 23-mer (ca. 100 μg) was hydrolyzed by a cocktail of snake venom phosphodiesterase and calf intestine alkaline phosphatase in 50 mM phosphate buffer (pH 7.2) at 37 °C for 5 h. The reaction mixture was passed through a membrane filter, and the whole filtrate was analyzed by HPLC on a Prodigy 5u ODS column (4.6×150 mm) at 40 °C, eluted with 50 mM ammonium formate buffer at a flow rate of 1.0 mL/min and detected at 260 nm. The following peaks appeared: cytidine (5.5 min), 6-formyl-2′-O-methylcytidine (7.4 min), guanosine (17.4 min), thymidine (22.8 min), and adenosine (46.9 min). Quanti-tative analysis for each nucleoside has not been done. The authentic sample of 6-formyl-2′-O-methylcytidine was synthesized from compound 7 via i) TBAF treatment to remove the TBDMS groups, ii) ammonolysis at 55 °C to convert the resulting 6-modified nucleoside into 6-(l, 2-dihydroxyethyl)-2′-O-methyl-cytidine (78%), iii) NaIO4 (1 eq) oxidation in H2O to obtain 6-formyl-2′-O-methylcytidine (65%). This compound cyclized to form intra-molecular hemiacetal between the 6-formyl group and the 5′-hydroxyl group, see
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