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RapidhydrolyticcleavageofthemRNAmodelcompound
# Supplementary Material (ESI) for Chemical Comunications # This journal is ? The Royal Society of Chemistry 2002 Rapid hydrolytic cleavage of the mRNA model compound HPNP by glycine based macrocyclic lanthanide ribonuclease mimics Thorfinnur Gunnlaugsson,*a R. Jeremy H. Davies,b Mark Nieuwenhuyzen,c Clarke S. Stevenson,b Raomain Viguiera and Sinead Mulreadya a Department of Chemistry, Trinity College Dublin, Dublin 2, Ireland. Fax: 00 353 1 671 2826; Tel: 00 353 1 608 3459; E-mail: gunnlaut@tcd.ie b School of Biology and Biochemistry, Queen’s University of Belfast, Belfast BT9 7BL, Northern Ireland. b School of Chemistry, Queen’s University of Belfast, Belfast BT9 5AG, Northern Ireland. Electronic supplementary information Synthesis of L and its lanthanide ion complexes. Glycine methyl ester (1) A solution of SM80 (1.6 g, 9.67 mmol) in dry acetonitrile (10 mL) was added to cyclen (0.405 g, 2.358 mmol), cesium carbonate (3.15 g, 9.67 mmol) and potassium iodide (1.6 g, 9.67 mmol) in dry acetonitrile (30 mL). This was then refluxed under argon for 48 hours. The mixture was filtered through celite and reduced before the residue was taken up in chloroform and washed with water. The organic layer was dried over K2CO3 and reduced to give a white hygroscopic powder. Yield: 69%; m.p. 161-163oC; Anal. Calcd for C28H48N8O12K: C, 46.21; H, 6.65; N, 15.37. Found: C, 46.64; H, 6.88; N, 14.95.; ?H (CDCl3, 400Hz): 7.8 (s, NH), 3.9 (2H, d, CH2), 3.6 (3H, s, CH3), 3.03 (2H, s, CH2), 2.6 (4H, s, cyc-CH2); ?C (CDCl3, 100Hz): 171, 170, 58, 52, 51, 40. M/Z: 689 (M+), 711 (MNa+); Acc Mass: 689.3470, IR?max(cm-1): 3435, 3071, 2956, 2824, 1749, 1672, 1543, 1439, 1439, 1369, 1310, 1214, 1096, 1003, 883, 806, 700, 589, 505, 378. Ln Complexes Lanthanide complexes were prepared by refluxing the ligand with 1.1 molar equivalents of the appropriate lanthanide triflate in dry acetonitrile (10mL) for 16 hours except on the case of the La(III) complex where dry methanol was used instead. Th
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