Tetraethylene glycol-derived spacer for oligonucleotide synthesis

Tetrahedron Letters

Volumn 39, Issue 35, 1998, Pages 6277-6280

  Gunzenhauser, Sigmund ^a   Biala, Ewa ^a   Strazewski, Peter ^a  

^a UNIVERSITY OF BASEL   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

MACROGOL DERIVATIVE; OLIGORIBONUCLEOTIDE;

ADSORPTION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; CROSS LINKING; HIGH TEMPERATURE; HYDROPHILICITY; MASS SPECTROMETRY; PHASE TRANSITION; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0032572868     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01348-3     Document Type: Article

References (14)

1. 1. Harris, J.M. Poly(ethylene glycol) Chemistry: Biotechnical and Biomedical Applications; Plenum Press: New York, 1992.
2. 2. Katzhendler, J.; Cohen, S.; Rahamim, E.; Weisz, M.; Ringel, I.; Deutsch, J. Tetrahedron 1989, 45, 2777.
3. 3. Schwabacher, A.W.; Lane, J.W.; Schiesher, M.W.; Leigh, K.M.; Johnson, C.W. J. Org. Chem. 1998, 63, 1727, and references cited therein.
4. 4. Kumar, P.; Ghosh, N.; Sadana, K.L.; Garg, B.S.; Gupta, K.C. Nucleosides & Nucleotides 1993, 12, 565.
5. 5. McCollum, C.; Andrus, A. Tetrahedron Letters, 1991, 32, 4069.
6. 3 (320.02); calc. C 30.03, H 5.04, O 15.00; found C 29.93/30.05, H 4.90/4.97, O 15.06/15.05.
7. 3 st sym.); 1125 (COC st as.).
8. 2 δ); 1120 (COC st as.).
9. 9. Mironov, V.F.; Sheludyakov, V.D.; Kozyukov, V.P. Zh. Obshch. Khim. 1969, 39, 2598-9 (Russ.); CA 1970, 72:66300r (Engl.).
10. 9. Mironov, V.F.; Sheludyakov, V.D.; Kozyukov, V.P. Zh. Obshch. Khim. 1969, 39, 2598-9 (Russ.); CA 1970, 72:66300r (Engl.).
11. 3 δ symm.); 1086/915/840.
12. 5 (244.25): calc. C 49.17, H 6.60, N 11.47, O 32.75; found C 49.28/49.24, H 6.75/6.69, N 11.51/11.49, O 32.51/32.51.
13. 2.
14. 2O; add 3 ml n-BuOH, precip. at -20°/0.5 h, spin down; dissolve each pellet in 600 μl HPLC buffer A; yields (crude): a) 52 OU, b) 39 OU. HPLC: column: Nucleogen® DEAE 500-7, 8 × 125 mm (Macherey-Nagel); buffer A: 20 mM Na/K phosphate, pH 7.0, buffer B: 0.6 M NaCl in buffer A; flow rate: 2 ml/min; gradient: 0 % B for 5 min., linear 0-80 % B within 15 min., isocratic 80 % B during 5 min., short wash-out at 100 % B; detection: 260 nm. Injection volume for depicted chromatograms: 5.0 μl each. Preparative separation on the same column using non-linear gradient; main product eluted under isocratic conditions at 67 % B. Isolated yields of full-length product: a) (10→) 33.2 OU, b) (12→) 23.5 OU.